


Check Yes, Juliet - High School AU

by ilikebigassbuttsandicannotlie



Category: SPN, Supernatural
Genre: Alternate Universe - High School, Alternate Universe- No Supernatural, Angst, Cop John Winchester, Dean and Jo are the same age, Established Relationship, F/M, Fluff, Friendship, Friendship/Love, High School, Highschool AU, Kissing, Making Out, Mary Winchester is still dead, Secret Relationship, Suggestive Themes, Tooth-Rotting Fluff, Underage Drinking, William Harvelle is still dead
Language: English
Status: In-Progress
Published: 2017-06-03
Updated: 2018-05-01
Packaged: 2018-11-08 08:42:48
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 12
Words: 21,391
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11078040
Author URL: https://archiveofourown.org/users/ilikebigassbuttsandicannotlie/pseuds/ilikebigassbuttsandicannotlie
Summary: Dean Winchester and Jo Harvelle secretly dating. 'Nough said.[Updated relatively regularly, you won't have to wait too long for more <3]Preview:"What are you doing here? I thought you were coming on Friday.""I am," Dean said, as he climbed through the window and into her room, "But I figured you'd have nothing better to do on a Tuesday night." He teased, and flashed her a smile."Well, I'm not the one who came all the way over here and climbed up to a second story window for no reason, so which one of us had nothing better to do?" Jo retorted."That's fair." He said, between a laugh.





	1. Testing the Waters

**Summary for the Chapter:**

> Backstory: William Harvelle and John Winchester were partner cops, and when Mary Winchester is murdered, John becomes obsessed with finding her killer and bringing them to justice. This leads John to making a risky decision on a case that gets Will killed. Ellen Harvelle never forgave him, and by extension, distrusts his sons.

It was quarter to 12am, Jo was at her desk, finishing the last bit of her homework. Trying to, anyway, at this point the words seemed like a whole other language. She groaned into her calculus textbook, and cursed herself for ever signing up for the class. Sure, the standard math class became too easy for her, but this was sheer torture.

A sudden knock at her window pulled her out of her thoughts. She pushed herself away from her desk, and stood to go open the window.

"What are you doing here? I thought you were coming on Friday."

"I am," Dean said, as he climbed through the window and into her room, "But I figured you'd have nothing better to do on a Tuesday night." He teased, and flashed her a smile.

"Well, I'm not the one who came all the way over here and climbed up to a second story window for no reason, so which one of us had nothing better to do?" Jo retorted.

"That's fair." He said, between a laugh.

"Seriously, though.. is everything okay?"

Dean shrugged, "Yeah, just... bad day."

Jo grabbed his hand and lead him to her bed, where they both sat. "What happened?"

"It's stupid.. forget I said anything."

"Tell me."

He let out a sigh, and laid on his back. "I got my report card today."

Jo mirrored him, and turned so she was facing him. "And?"

"And I got a D on everything except my English class, which I failed."

"Well.. It's not that bad, you still have time to make it up!"

"I guess.." He sighed, "I told my dad it hadn't come yet. He's not gonna care if I can make it up, all he's going to focus on is how bad it is now."

"Oh.."

"Yeah."

"Maybe I can tutor you. You're so smart, Dean. I think you just need help to catch up." She placed a hand on his bicep and smiled at him.

Dean smiled, turned on his side, and pulled Jo close to meet their lips. He caressed her cheek then made his way to tangle his hand in her hair. Their lips mingled in a soft, tender dance, and the world slipped away from them. Her lips tasted like vanilla chapstick, and Jo could tell he'd had beer earlier.

They stayed like this for awhile, until Jo pulled away. She pushed Dean's chest lightly so he laid on his back, and she cuddled against his chest.

He wrapped his arms around her, and Jo sighed, "I wish you could stay all night.." She said as she drew invisible shapes in the fabric of his cotton shirt.

Dean chuckles, "Yeah me too, except I don't want to wake up dead, brutally murdered by your mom."

"Drama queen. What's the worst that could happen? She'd call your dad."

"Oh god, I'd rather she'd kill me."

"Again. Dramatic."

"I wish I was being dramatic," He stated, with a slight smirk on his face, which faded as he turned his gaze away from her and up at the ceiling.

Dean could see in his peripheral vision that she was staring at him, and after a moment she asked, "What's so bad about your dad?"

A long silence followed her question. "Can we talk about something else?" He asked finally, without looking over at her.

His voice was low and soft now, and a small pit grew in Jo's stomach, she wished she had just left him alone. "Do you wanna watch a movie?"

Dean sat up with his elbows and flashed her a smirk, "Only if I get to pick."

"Go for it. Nothing too loud, though. Unless you want to get murdered." She teased, and he laughed, pushed himself off the bed, and sat in front of her tv where she kept her movies.

"Oh god, Jo, Footloose?" He said, holding the movie up and looking back at her incredulously.

"Shut up! It's a good movie!" She protested, and he rolled his eyes in response and continued rifling through her collection.

They eventually decided on The Breakfast Club, both sat with their backs against the headboard, and hands intertwined as they watched.

Not even 20 minutes in, Jo was nodding off against his shoulder. Dean smiled, and placed a soft kiss on her temple. She stirred, fluttering her eyes open and gazing up at him, "Did I fall asleep?"

"Yeah... you looked pretty cute, though." Jo was a little surprised by his remark, he was probably too tired to say something sarcastic instead, she thought. "I should go. You need your sleep."

"No, no, I'm fine. Stay."

"Jo." His stare mimicked her mother when she refused to do a chore.

"Fine..." She conceded and he planted a soft kiss on her lips before he pushed himself off the bed, "See you tomorrow," Dean flashed her a smirk before he clambered out her window.

Jo met her mother in the kitchen for breakfast the next morning.

"Good morning," Her mother greeted.

Butterflies swarmed in her stomach at the thought of actually asking but she took a deep breath and went ahead anyway. "Hey, mom?"

"Yes, sweetheart?" Ellen answered, without turning away from the meal she was preparing.

"Um... I was wondering if Dean Winchester could come over after school."

Ellen turned down the burner and turned to her, "Why?"

"I was going to tutor him... Kinda already told him I would..."

Her mother sighed, "You shouldn't have promised that, Jo. You know how I feel about them."

"I know how you feel about John but you don't know anything about Dean."

"I know plenty about him, and I don't think you should hang around him. He's a bad influence."

Jo exhaled, "What exactly makes him a bad influence?" She said, air quotes surrounding 'bad influence.'

"Let's see, he drinks, he goes through girlfriends like they're tic tacs; and I use the word 'girlfriend' generously, he's been arrested on several occaisions, need I go on?" Ellen argued, her hands fixed on her hips.

Anger boiled in Jo's chest, "He's not as bad as you make him out to be!" She shouted.

"Don't you yell at me, Joanna." She said, her voice hard and stern. "And since when are you best friends with Dean Winchester?"

"I gotta go." Jo grabbed her backpack and shoved her feet in her shoes, before she slammed the front door behind her.

When Jo arrived at school, she made a beeline to her locker, where she found her boyfriend leaning against, waiting for her.

"Hey." She greeted flatly as she began to unlock the combination.

"Are you okay?" He pushed himself forward and turned to her, placing a hand on her back.

"No." She grabbed her books before closing her locker and making her way down the hall, Dean followed suit.

"What happened?"

"I tried to ask my mom if you could come over after school so I could tutor you."

"What did she say?"

"She's being really unfair. She said you're a 'bad influence' and I shouldn't hang around you."

Dean shoved his hands in his pockets, "Oh.."

Jo exhaled, "Do you want to meet in the library after school? We can study there."

"I can't today. I gotta take Sam to soccer practice."

She opened her mouth to speak but was interrupted by the bell ringing, and they both went their separate ways to class.

Jo stepped inside her front door, shrugged her backpack off, and pulled off her shoes before making her way upstairs.

"Jo?" Her mother called from her bedroom, "Could you come here for a minute?"

She did as she was told, and met her mother in her room, where she was folding laundry.

"Jo... Can we talk about this morning?"

She sat on the bed shyly, unknowing of what to expect, "Okay.."

"Do you like him?"

"No." She defended, and her mother gave her an inquisitive look.

"You can tell me, I won't be mad."

Jo could hardly believe what she was hearing. "Yes.."

"Look... I get it. I was just like you when I was your age, the whole bad boy thing was very hot. But.. it'll only end in heartbreak, and I just don't want you getting hurt."

"He wouldn't do that, mom. He might get into trouble sometimes but he's a really good guy. He has a sweet heart." Jo explained, and her heart began to flutter at the thought that she might actually approve.

Ellen took a deep breath, "If you're really certain... then I guess tutoring him here wouldn't hurt."

Jo grinned widely, "Really?"

"Yes."

She pulled her mother in an embrace, "Thank you.."

Ellen smiled softly, wrapping her arms around Jo, "You really like him, don't you?"

"I don't know..." Jo pulled away from her, turning her head away to hide her blush. She wasn't used to talking to her mom about crushes. Especially when it came to Dean.

"Sweetheart..." Ellen placed a hand on her knee and Jo turned to her, "Just be careful, okay?"

"I will, mom."


	2. Second Chances

**Summary for the Chapter:**

> Dean formally introduces himself to Ellen, Jo starts tutoring Dean, and he has an alternative plan for Friday night.

**Notes for the Chapter:**

> Hey, guys!! Please let me know what you think!!
> 
> If you have a favorite part or any suggestions, leave me a comment! I'll read and reply to all!

After her mother had gone to bed, Jo grabbed the phone and dialed Dean's home phone.

"Hello?"

"Hey," Jo whispered, "Good news."

"You're finally getting facial reconstruction surgery?"

"Hilarious." He laughed and he could practically hear her rolling her eyes. "Come on, I'm serious."

"Okay, fine. What is it?"

"My mom said I can tutor you here after school."

"Seriously?" He enthused, "How did you manage that?"

"I'm awesome, that's how."

"You really are."

Jo smiled at his words, and felt a rush of heat to her cheeks. "S-so how was Sam's soccer practice?"

Dean chuckled to himself, he could tell she was flustered. "Good, he did great."

"That's good.. Does your dad know about your report card yet?"

"Your smalltalk sucks." He joked. Jo heard another voice in the background, that she figured must be Sam's, "Hey, I gotta go." He told her, and they said their goodbyes and hung up.

Sam looked up at his brother inquisitively, "Who was that?"

"A friend."

"At 10pm?"

Dean strolled back over to the living room and plopped on the couch. "Yep."

Sam followed and sat beside him, "Was it your girlfriend?" He nudged his arm and grinned.

He remained silent, fixated on the tv.

"You didn't say noooo." His little brother teased in a sing-songy voice.

"Shut up, Sam."

"What's her name?"

"I swear to god..."

"Come on, who is it?"

Dean sighed, "I'll tell you as long as you promise not to tell anyone. Okay? Not even dad."

"I promise!" Sam held out his pinky to make the promise official, and they carried out the pinky swear.

"Okay.. It's Jo Harvelle."

Sam inhaled, "Whoa, really? Doesn't her mom like.. hate us?"

Dean shrugged, "Kinda, yeah... Jo's warming her up to the idea, though."

"How long have you two been dating? And how does her mom not know?"

"A few months.. And uh.. I've been sneaking over to her house once or twice a week."

"How do you get in without waking up her mom??"

"I climb up to Jo's bedroom window."

"Wow... that's badass." Sam beamed at him, "You're like Batman."

Dean smiled, "Thanks, dude.. Hey, it's getting late, you should get to bed. Dad's gonna be home in an hour and it's my ass on the line if you're still awake." He stood and turned off the tv.

"It's only 10!" Sam whined.

"I don't make the rules, Sammy."

Sam groaned as he made his way up the stairs and Dean followed after switching off the lights.

The following morning Dean went on with his morning routine of waking Sam and brushing his teeth before heading downstairs for breakfast.

"Morning." Dean greeted his father, who was sat at the kitchen table with a coffee and the day's newspaper.

"Mornin."

Dean started rifling through the fridge and his father put down his paper, "Did you get your report card yet?"

His heart started to race, and he took a deep breath, "Yeah, yesterday.. I'll go get it."

He fetched it from his backpack by the door, and returned to the kitchen, holding it out for his father, "Um.. Before you say anything, I'm getting a tutor and this won't happen again. I swear."

John looked at him inquisitively and a pit grew in Dean's stomach as his father opened the card.

"I don't believe this. All D's and an F, Dean, are you kidding me?" He said, his voice starting to raise at the end of his sentence.

Dean stood silently as his father continued his lecture for the next half hour, until John had to leave for work. He grabbed his backpack and slipped his shoes on before heading out the door.

He got to school well past 7am, and shoved his pink tardy slip in his pocket before getting to his locker.

As he stepped into English class, the teacher stopped her lesson, "Well, thanks for daining us with your presence, Mr. Winchester."

"Charming as always, Ms. Campbell, how is it that you're still single?"

The class roared with laughter, "Take your seat, Dean." She said sharply.

He slumped in his desk chair, and tried his best to pay attention to her droll on about... Well, whatever it was she was talking about, but it was all just noise.

His eyes wandered to the window to his left. Wispy clouds peppered the bright blue sky, and he began to wonder what Jo was doing.

She'd be in History. Probably taking notes right now. She has such nice handwriting. Much better than his. What is she wearing today? It doesn't matter, she always looks cute. "You should be paying attention, Dean." He could imagine her saying, and guilty, he turned his attention to Ms. Campbell. Dean opened his notebook and started jotting down the lesson.

The bell rang shortly after, and he shut his books before going strolling to his locker.

"Hey!" Jo greeted, catching up with him. "Where were you this morning?"

"I was late." He said, trading his English books with his Math ones.

"How come?"

Dean shut his locker, "I showed my dad my report card.. Needless to say, I'm grounded."

"For how long?"

He shrugged in reply and leaned his back against the locker.

"Can you still come over after school?"

"I'll have to ask," He crossed his arms, "I told him I was getting a tutor but we never got to talk about it.." He paused, "What should I wear?"

She raised a brow at him, "What do you mean?"

"I mean if I come over.. I don't think this-" He gestured to all of himself, "-will work.. I want to make a good impression."

Jo looked his outfit over as he spoke; he was wearing a black Led Zeppelin tee, worn jeans, and a pair of beat up red sneakers. "It'll be fine. You don't have to show up in a tuxedo or anything." She joked, nudging his shoulder as she flashed him a smirk.

"Thanks," He planted a kiss on her lips before the bell rang and they headed to their respective classes.

Dean tossed his backpack on the floor as he walked inside, "Hey, dad?"

"I'm up here!" He called back.

Dean slid off his shoes before heading upstairs. "I was wondering..." He started, as he entered his father's bedroom at the end of the hall. "You know Jo Harvelle?"

John looked up from the paperwork cluttered all over the bed, "Will and Ellen's daughter?" Dean nodded in reply, "What about her?"

"Well... we're kinda good friends and she offered to tutor me." He rubbed his left bicep with his right hand as he spoke, "I know I'm grounded, but.. would that be okay?"

"Ellen is okay with this?"

"Yeah! You can call her if you want."

John smirked, "You two always did get along... I think that's a good idea." He shot him a warning glance, "As long as Ellen is home, too. Hands to yourself, alright?"

"Okay, dad.." Dean rubbed the back of his neck, hoping the heat in his cheeks wasn't noticable, "So, um... Can I go over right now? Jo said it was okay."

"Go ahead, son.. But I mean it, best behavior, okay?"

"Yes, sir. Scout's honor." He flashed him a smile before making his way downstairs and out the door.

Dean's heart raced and palms perspired as he stepped up to the Harvelle's front door. Sneaking in, he was used to, but being invited and actually talk to Ellen? A whole different ballgame. He had to pay attention to every movement, and think out every word.

He took a deep breath in, and knocked on the door.

It only took a few moments before the door opened, revealing Ellen behind it.

"Good afternoon, Mrs. Harvelle." He flashed her a charming smile.

She smiled softly, "Good afternoon to you, too, Dean. Come in." She held the door open and he stepped inside.

He slipped off his shoes, "Sorry I didn't call first.. it totally slipped my mind."

"It's alright," Ellen closed the door behind him, "Jo told me you might be coming. She's in the dining room."

"You have a beautiful home, Mrs. Harvelle.. It hasn't changed a bit, huh?"

"You remember it?" She laughed, "You and Jo used to have playdates all the time. The crazy shenanigans you two got into..."

He chuckled, "Yeah.. I remember coloring on these walls."

"Mhmm.. More than once."

Ellen ushered him into the dining room, and he set his backpack on the table and sat next to Jo.

"Let me know if you two need anything. I'll be upstairs." Ellen said, before leaving the room.

"I'm glad you could come." Jo smiled at him, "Okay, what subject do you want to start with?"

"Lunch?"

She chuckled, "Come on, Dean. How about math?"

He groaned, "Do we have to?"

"It'll be fine.." She unzipped his backpack and began digging through it, "Geez, your backpack is cleaner than mine.." Jo then pulled out his math textbook, "Which one is your math notebook?"

"The blue one."

She set the notebook on the table, grabbed two pencils, and opened the textbook.

Dean smiled softly as he watched her lips move along as she read, trying to find the right page.

"Okay, here it is. Ready?"

Jo watched his eyes dart up to meet hers. "Pay attention." She said, nudging his shoulder, "My eyes are up here."

She started to read aloud the lesson to him, and he hung onto her every word. She explained each step, and he soon caught on like wildfire. They blew through the rest of the assignments, Dean started packing away his books.

"So..." He zipped up his backpack and leaned back in his chair, "I know I was going to come over Friday but.. a buddy of mine is having a party and I thought maybe we could go."

"You know you're still grounded, right?"

"Yeah," Dean shrugged, "my dad is visiting his friend out of town tomorrow morning. He won't be back til Saturday." He flashed a smirk at her.

"Dean.." Her voice apprehensive, "I don't think that's a good idea."

"Why? He's not gonna know."

"What if he comes home early? Or if he calls to check on you guys?"

"Wouldn't count on it. Come on, it'll be fun."

"Famous last words."

"Jo, it's gonna be fine. I wouldn't get you in trouble on purpose."


	3. The Party

**Summary for the Chapter:**

> Jo reluctantly agreed to go to the party, and it turns out to be a bit more than she bargained for.
> 
> (I apologize, I can't make the summary any longer without spoiling.)

**Notes for the Chapter:**

> Hey, guys!! Please let me know what you think!!
> 
> If you have a favorite part or any suggestions, leave me a comment! I'll read and reply to all!

After some persuasion, Jo reluctantly agreed to go to the party. She had told her mother she was going to her friend's house, and promised to be back by eleven. Luckily, Sam was spending the night at his friend's, and Dean didn't have to come up with an alibi for him.

Jo waved goodbye to her mom before stepping off the porch and heading down the sidewalk.

She turned the corner and nearly crashed into Dean. "Geez, you scared me!" She said, holding her hand to her heart and catching her breath.

He laughed, "Man, I wish I had a camera."

"Jerk." She gave him a punch in the shoulder, "What time is the party?"

"Nine." He shoved his hands in his pockets as they started walking.

Jo checked her left wrist, forgetting she wasn't wearing a watch. "What time is it now?"

"Nine."

She looked worried, so he elaborated, "Rule one to parties: never show up on time."

"Why not?"

"I dunno it's just.. a rule."

After an hour or so, they both sat on the steps of the deck to get away from the noise and crowd. Jo took a sip from her solo cup and turned to Dean, "Can I ask you something?"

"Shoot."

"How come you never talk about your dad?"

Dean took a long sip of his beer and remained silent. Jo reached out and grabbed his hand, rubbing her thumb across the back.

"What does it matter? It's not like you talk about your mom all the time."

"I'm just worried about you.."

He finished off the rest of his drink, "I'm fine." He crumpled his cup before tossing it in the yard, "Wanna go inside?"

Jo mirrored his movement, "No. Talk to me."

Dean pulled his hand away and crossed his arms over his chest, "What do you want me to say, Jo?" The alcohol had began taking effect, his mental filter fading away.

"I just want you to be honest with me."

"Why? So you can fix me?"

"Dean, stop! You know that's not true!"

"Then what is it, Jo? I mean, hell, I'm such a fuck-up your mom can't even know we're dating!" He swung his arms up as his last word escaped his lips, his eyes getting misty.

"Dean.." She held his hands, pulling him close, "I love you. I don't care what anyone else thinks of you because I know who you really are. You're smart, you're funny, and you have the biggest heart of anyone I know; you put everyone else before yourself. That means something."

Jo brushed away a stray tear with her thumb before he pulled her in an embrace. He placed a hand just above the nape of her neck, the other on the curve of her back. "I love you, too."

Jo wrapped her arms around his torso, nuzzling against his shoulder. "I'm sorry I pushed you.. this was supposed to be a fun night and I ruined it."

"You didn't, babe. It's fine." He pulled away enough to look her in the eyes, "Do you wanna go back inside?"

She nodded, and they went back in, hand in hand.

"Hey, Dean!" A voice called out from across the dim room, "C'mere!"

The voice led them to the pool table in the adjacent room, where a crowd had gathered.

Dean then put the voice to a face, it was the host, Jake Miller. "Hey, dude!" Dean greeted him. They shook hands, pulled each other in for a one-arm hug, and pat each other on the back before pulling away.

Dean and Jake were good friends, Jo surmised that they probably went to parties together a lot. She didn't know Jake, aside from seeing him in the hallway or talking to Dean from time to time. If Dean trusted him, she figured he must be a good guy, then.

"Hey, Jo!" Jake welcomed before turning to Dean. He smirked as he whispered something in Dean's ear, granting him a punch in the arm, "Dude, come on, that's my girlfriend."

Jake snickered, "Sorry.. anyway I'm glad I found you, we could use you to show these jokers how this game is really played."

Jo scanned the room. The dining room table was missing the chairs, and two pairs of 10 cups each were filled to the brim and set up in a pyramid shape on either sides the table. "Beer pong?" She inquired, looking between the boys.

"Yep! Your boyfriend here is the king of beer pong." He stated proudly, throwing an arm over Dean's shoulder.

She quirked an eyebrow and flashed him a smirk. "Well, I'd love to see the king in action."

"Yeah, Dean, show your girlfriend your amazing talent." Jake encouraged, shaking his shoulders.

Dean smiled, "Alright, one round!"

They decided on teams of two, their team being Dean and Jo, and their oppenents were Dylan Masters and Greg Lowe; couple of guys on the football team.

Dean stepped up to the table. He held the ball between his middle finger and thumb, his tongue poking out the corner of his mouth as he aimed.

He arched the ball and it landed dead center into the middle cup. "See!! What did I tell you!!" Jake enthused, gesturing to the cheering crowd.

It was now Jo's turn. Her heart rate increased as she stepped up to the table. Dean placed a hand on her lower back and whispered in her ear, "It's okay, you got this. The key is to aim for a specific spot and arch it. Just a flick of the wrist."

She nodded, and followed his advice. She missed just by a hair, and it fell to the floor.

She groaned, and it was now their opponents turns. They both got a cup, and Dean and Jo drank one each.

They played for about 20 minutes before Jo could feel the drinks starting to really effect her.

Their team had four cups left, their opponents only having one. Dean stepped up, and his ball rolled around the rim for a second before falling into their cup.

The crowd cheered, and Dylan pouted, crossing his arms and rolling his eyes.

Dean grinned, "Man, I thought you guys were just bad at football but I guess you can't throw any ball."

"Fuck you, Winchester!"

Dean laughed and Jake intervened, "Alright guys, take it easy. Dean, can I talk to you outside for a minute?"

He followed Jake, and Jo stayed behind, feeling a bit awkward that she didn't know anyone here.

Jake shut the back door behind them, "What is the matter with you?"

Dean furrowed his brows, "What are you talking about?"

"I mean why are you trying to pick a fight with those guys?"

"That's what this is about?" He rolled his eyes, "Geez, Jake, I was joking."

"Yeah, well, they were ready to kick your ass. They still might."

"Whatever." Dean reached for the doorknob but Jake blocked him.

"Seriously. Don't start any fights. I can't have the cops showing up, I'll be grounded for the rest of my life."

"Okay mom, I'll be good."

Jake chuckled as they headed inside. He went into the bathroom, and Dean made a beeline for the dining room, that was until Dylan blocked his path, "You think you're hot shit, don't you?"

"Look, dude, I was just kidding around. I'm sorry. Are we good?"

"Fine. But you're on thin ice, Winchester."

"Okie dokie." He past him and rejoined Jo, who had found a couple of friends.

She smiled at him, "Hey! Dean, these are my friends, Lydia and Ashley."

He shook their hands respectively, "Nice to meet you both."

"You're even nicer looking in person. I-I mean you're even nicer in person." Lydia stammered.

Dean chuckled, "Thanks. Back at'cha."

"So your mom really doesn't know you two are dating?" Ashley asked.

"Yeah.. she's warming up to him, though." Jo smiled at him.

"So you're like Romeo and Juliet then, huh? That's pretty romantic."

"Yeah, I guess we are.." Dean smirked, "I mean, before the suicide part."

Ashley furrowed her brows, "What are you talking about?"

"Romeo and Juliet. They commit suicide together at the end. Haven't you read it?"

"Yeah, I guess I forgot that part..."

"You're such a nerd." Jake shoved Dean playfully as he entered the room. "Ah, shit I forgot, hang on."

He left for a moment and came back with two full cups of beer, handing one to Dean and keeping the other.

"Oh, so that's why I keep you around." Dean jested before taking a long sip.

"You want one, Jo?" Jake asked.

"No, thanks." She was starting to feel a bit nauseated, but tried her best to ignore it.

Jake and Dean continued talking for 15 minutes or so, every drink Dean finished, Jake refilled, and he was 3 drinks down when he started to get tipsy.

"Jo.." He stumbled for a second, and leaned against her for balance, "Ha-have I told you how cute you are?"

She wrapped an arm under his right arm and over his left shoulder to steady him, "Come on, we should sit down." She guided him to the couch in the living room.

They both sat down, and Dean started playing with her hair. He giggled, "Your hair is so shiny... how do you do that?"

Jo chuckled and smiled at him, "You're pretty cute like this. Maybe you should be drunk all the time."

"I agree." He paused for a minute before leaning against her, shutting his eyes, "Sleepy."

"You wanna go home?"

"No."

She placed a soft kiss on the top of his head, "I'm gonna get you a glass of water. Stay here, okay?"

He nodded and she carefully scooted off the couch, and gently laid him down as to not disturb him.

When she returned, he was still laying peacefully, half-asleep.

"Here, sit up." She instructed.

He reluctantly cooperated and she handed him the glass. When he finished, he set it on the table beside him. Jo refilled it, and when he finished she refilled it again, and he started to sober up.

"We need to go soon. It's 10:30."

"Ugh.." Dean laid his head back on the cushion. "Hey.." He said as he got an idea, turning to her, "What if you asked your mom if you could stay the night at your friend's house? My dad won't be home til morning, you can stay with me."

Jo quirked an eyebrow at him, giving him a questioning look.

"What? OH- N-no I'm not trying to proposition you or anything.. I thought it could be fun, though. We have popcorn."

She smiled, "Only if I get to pick the movie."

"Fine by me. We don't have any chick flicks." He teased.


	4. Sleepover

**Summary for the Chapter:**

> Dean and Jo have a sleepover! Tooth-rotting fluff ensues.

**Notes for the Chapter:**

> Special thanks to my best friend, and @warqueenfuriosa for being my personal cheerleaders through this, being wonderful friends .｡.:*☆
> 
> Hey, guys!! Please let me know what you think!!
> 
> If you have a favorite part or any suggestions, leave me a comment! I'll read and reply to all!

Dean pushed off his shoes with his feet when they entered his house. He took Jo's coat off for her and hung it on the coatrack, "Would you like a tour, m'lady?"

He grabbed her hand and kissed the back and Jo chortled, "So chivalry isn't dead."

After showing her a brief look at the house, he lead her up to his bedroom and held the door open for her. Jo stepped inside, and started looking around as Dean rifled through the closet for his movie collection. Rock posters were peppered on the walls and a milk crate filled with records sat on the desk.

An old photo framed on his night stand caught her eye. She picked it up and gave it a long look.

"Is this your mom?"

Dean looked over his shoulder to see what she was asking about, "Yeah."

"Awww and is that you? You look so cute!! How old are you here?"

He shrugged, "Three or four."

Jo smiled fondly at the picture. It showed his mother hugging him in front of their house. "She's beautiful."

Dean smiled to himself, "Yeah.. she was."

"You should've kept the bowl cut. It was a good look." She jested.

He laughed and she set down the picture and joined him in front of the closet, "So what movies do you have?"

"Take your pick." He slid the cardboard box over to her.

Jo sat on the floor and started digging through them.

"We should marathon a trilogy!" Dean suggested, sitting himself next to her, "I have Star Wars, Star Trek, Indiana Jones, Die Hard, Back to the Future.."

"Nerd."

"Come on, pick one! It'll be fun!" He enthused, "I'll go get us snacks and drinks."

He came back five minutes later with his arms impossibly full with chips, popcorn, candy, a 2-liter of soda, and two glasses. He shuffled past her and dropped everything on the bed, not including the glasses, which he set on the nightstand.

"Alright, what are we watching?" He asked without skipping a beat.

"Duh, Star Wars." Jo replied as she put the tape in the vcr. She stood and was about to sit on the bed when Dean blocked her.

"Wait wait wait I need to get it set up first. Close your eyes."

"What?"

"It's a surprise. Close 'em!"

She reluctantly complied and a few minutes went by before she could open them again.

When she did, she saw he'd turned off the lights, and had a mountain of pillows for them to sit against. The snacks were neatly arranged at the foot of the bed, all opened and facing the headboard. Dean was laying on the near side of the bed, and left extra blankets for her on the opposite side.

Jo smiled as she settled into bed. She scooted closer and placed a hand on his cheek before touching her lips to his. Jo was slow and Dean was fast, polar opposites colliding together but they made it work.

Jo tangled her hand in his hair and he unconsciously bit her lip as a reaction. She hummed, parting her lips so he could deepen the kiss. His tongue delve in and moved slowly before they found their rhythm. Dean laid his hand just above her knee. Knowing her boundaries, but deciding to test them, he slid his hand higher, tightening his grip slightly.

Jo grasped his wrist, sliding his hand underneath her shirt when the blaring fanfare of the movie's intro theme started, causing them both to jolt apart at the surprise.

They both readjusted themselves to watch the movie. They were silent for awhile, awkwardly aware of what might've happened, had they not been interrupted.

Dean finally broke the silence, "Are you hungry?" Gesturing towards the buffet of snacks.

"Actually, yeah." She reached and grabbed the popcorn bag. She tuck herself under the covers, and turned to Dean, "Are you going to sleep in your clothes?"

He looked down at himself, "Oh, yeah I guess I should change."

Jo already had when they stopped at her house to ask her mother if she could stay the night at her "friend's". He pushed himself off the bed, and began rummaging through his dresser that the tv was sat on.

"Hurry up, you're in the way."

"I'm going, I'm going." He grabbed a t-shirt on the way out of the room. He came back a moment later, wearing his crimson plaid pajama bottoms and a plain black shirt.

Jo was looking him up and down before he cozied himself under the covers. He quirked an eyebrow at her, "What?"

"Nothing.." She turned back to the tv, smiling to herself.

"What is it?"

"I've never seen you in pajamas before.." She shrugged, "It's cute."

He smirked at her, wrapping an arm around her and she leaned into it, snuggling against his chest. Dean grabbed a handful of popcorn from the bag she was holding as they watched.

After a long while Jo reached out her arm, "Drink, please."

He handed her a glass and filled it with soda, and poured himself a glass too.

Dean began playing with her hair, twirling a soft strand in his fingers. Jo set the popcorn aside and wrapped an arm around his waist and he felt a warm flutter in his chest.

They were soon interrupted when he heard the front door close. Dean quickly shuffled out of the covers and out of bed, "Shit. Someone's here." He turned back to Jo, "Stay here." He told her before he went out the door, shutting it behind him.

Dean's heart raced out of his chest as he hurried down the stairs, silently praying it wasn't his father. As he turned the corner in the entryway to the living room, he was relieved to find it was Sam.

"What are you doing home?"

"Greg got sick, so his parents sent me home." He shrugged as he stood from the couch and made his way into the kitchen.

Dean followed, "Oh.. it's pretty late, though. You should go to bed."

"Why?" Sam asked as he refiled through the pantry, "Dad's not here and it's Friday. Plus I'm wide awake... ugh, did you eat all the chips? They were here this morning."

"No, they're in my room."

"Jerk. You're always hogging them!" Sam said as he started to pass his brother out of the kitchen before Dean grabbed his arm to stop him, "I-I'll get them. Don't worry about it."

Sam pulled his arm away, "Geez, what's your problem?"

"Nothing.. it's just my fault they're in there so I'll grab 'em for you."

"Okay.." Sam said skeptically before grabbing his backpack and heading up the stairs, Dean trailing close behind him.

"Are you watching a movie?" He asked, hearing the noise coming from Dean's bedroom.

"Yeah.. you wouldn't be interested. You should probably go unpack."

Sam stopped and listened closely, "Is that Star Wars?" He enthused, and entered his room.

"Jo??" His jaw dropped and he turned to his brother, "You brought Jo here??"

"Hi, Sam." Jo smiled awkwardly at him.

Dean sighed, "Yes, now just take the chips and get out."

"Can I hang out with you guys? You have all the snacks and I wanna watch Star Wars too!"

"No. We can watch Star Wars tomorrow, go to your room."

"Pleeease? Otherwise I'm telling dad." Sam threatened, crossing his arms.

"Are you seriously blackmailing me so you can watch Star Wars?"

"Yes. And I mean it."

Dean sighed heavily, clenching his jaw. "Fine.. shithead."

Sam smiled and climbed onto the bed, grabbing a few bags of chips and candy. Dean settled back into bed next to Jo, and Sam squeezed next to him, making him scoot over so there was more room.

Jo grabbed Dean's hand, holding it as she leaned her head against his shoulder.

Sam grinned, looking between both of them, "You guys are cute."

"Thanks." Jo smiled, and Dean remained silent, trying to fixate on the movie instead of how much he hated his little brother right now.

"So... you guys weren't like... doing stuff before I got here, were you?"

"Doing stuff?" Jo questioned.

"Like... sex."

"Oh my god, Sam, no!" Dean said, "How do you even know what that is?"

"I'm twelve, Dean. Plus, I know you've done it before."

Dean buried his face in his free hand, "Please. Stop. Talking."

"Fine.." He said before shoving a handful of candy into his mouth.

"Sorry about this.." Dean whispered to Jo.

Jo chuckled quietly, matching his volume, "It's fine. I think it's the sugar."

It wasn't long before the sugar caught up to him, though, and he crashed at the beginning of the second movie, dozing off on Dean's shoulder.

Jo smiled at his little brother, "Awww. That's so sweet."

"Yeah, he looks pretty cute when he's not being an asshole." Dean nudged him lightly, "Sam," He called in hopes it would wake him, "Come on, you need to go in your own bed."

Sam groaned and rested his head on a pillow at Dean's side.

"Am I gonna have to carry you?"

He nodded in reply, causing Dean to let out a soft sigh before pushing himself off the bed. He slid his hands underneath his brother, lifting him and carried him to his room bridal style.

Jo smiled at this, it being very reminiscent of her father when she was little and she was too tired or just refused to go to bed on her own. Her mind then began to unconsciously wander. Dean would be an amazing father. Soft and kind, but tough when he needed to be. He'd be such a fun dad, too. Joining in on their games, making them laugh when they're upset. She quickly shook the thought out of her head as he reentered the room, settling back into bed beside her.

"So.. now that he's gone..." Dean flashed a mischievous smirk before he leaned in to close the distance between them.

Jo smiled against his lips, and melted into the kiss. Their lips argued over who took the lead, until Dean moved his head to her neck, peppering kisses along the curve. She couldn't help but giggle at the light touches, and his lips joined hers again. Dean rolled himself so he was hovering over her, and tangled a hand in her hair, while the other laid beside her on the bed, keeping himself steady.

She pressed her hands against his chest, pushing him back enough to break the kiss. "Dean..." Jo paused, her eyes focused on her hands, "I don't think we should go further than this.."

"Okay."

His response threw her off-guard, "That's it?"

"What?"

"I dunno.. I kinda expected you to be mad..."

Dean almost laughed at her reply, "Mad? Jo, I get it..." His voice was soft now and he moved his hand from her hair down to her cheek, "You don't have to do anything you're not comfortable with, alright? All you have to do is say so."

Jo smiled and pulled him in for a hug. She didn't think it all the way through, though, as she caused him to fall and his weight pushed the air out of her lungs.

Dean quickly pushed himself up with his arms at each side of her, holding in his laughter, "Are you okay?"

"I'm fine.. you should lay off the cheeseburgers, though." Jo teased with a cheeky smile on her face.

"Shut up." He said between a laugh.

"So what I was going to say before you crushed me..." She placed a hand on the nape of his neck and pulled him down to meet their lips before she continued, "What did I do to deserve you?"

In the moment, his instinct was to say some sarcastic remark, but failed to come up with anything. Instead, he couldn't help but grin widely at her words. It never occurred to Dean that anyone would ever see him that way; as something of a dream, too good to be true.

Jo brought her hand to caress his cheek, her thumb tracing an invisible line back and forth across his cheekbone.

They stayed that way for quite a few minutes, just gazing at each other, neither feeling the need to fill the silence. He thought about how gorgeous her brown eyes are; especially now when the light made them a shimmering amber. She thought about how stunning his green eyes are, like lush emerald fields with hints of gold in them. But what they both really loved is how their eyes tell the stories their mouths fail to, and how in moments like these they don't have to say anything.

"Hey, lay down." Jo eventually said, and he complied.

She slid across to him, resting her head against his chest, wrapping her arms around his torso. He laid his arm along her back, and sighed contentedly, "My life would really suck without you."

"Back at'cha, big guy." Jo said lazily, as she started to doze off.

Dean leaned over carefully, as not to wake her, grabbing the tv remote and switching it off. He settled back into the pillows, and soon drifted off himself.


	5. Like Icarus...

**Summary for the Chapter:**

> Dean and Jo accidentally sleep in too late and end up getting caught, and John has an announcement to make regarding his trip.

**Notes for the Chapter:**

> Hey, guys!! This has almost gotten 100 hits, wow! Please let me know what you think!!
> 
> If you have a favorite part or any suggestions, leave me a comment! I'll read and reply to all!

The following morning, they were in completely different positions; Dean laid on his stomach, and Jo was curled up on her side facing towards him, their legs tangled together.

Dean fluttered his eyes open when he heard a knock on his bedroom door.

"Dean? Are you up?" His father's voice called the hallway.

"Oh, fuck." He whispered to himself as he hastily shuffled out of bed, "Uh, just a second! I'm getting dressed!" Dean called back.

He nudged Jo awake, "Jo, you gotta get up," he whispered, "Don't move, okay?" She opened her mouth to protest but Dean interrupted her, "Trust me."

Jo nodded, and he pulled the covers over her head, piling some pillows haphazardly on top of her; creating the illusion that he was alone.

Dean quickly threw on some clothes before opening the door, "Hey, how was your trip?"

"Good." John smiled, "It sounds like you and Sam had a good time, too."

His heart raced and he tried to hide it with a smirk, "What did Sam say?"

"Just that you stayed up half the night watching Star Wars."

Dean chuckled as the relief washed over him, "Yeah.. it was pretty fun."

They stood in silence for a moment, Dean fidgeting the placement of his feet nervously with his hand glued to the doorknob; hoping his father wouldn't hang around his room much longer.

John furrowed his brow, "Are you coming downstairs?"

"Yeah.. I'm gonna clean up my room a bit, first. We kinda left it a mess last night."

"Alright, see you in a bit."

After he left, Dean closed his door and returned to Jo, who'd already dug herself out of the pillow and blanket mound.

"How am I supposed to get out of here?"

He rubbed the nape of his neck anxiously, "I uh... I don't know.. there's always the window."

She quirked an eyebrow incredulously, "I'm not doing that."

"It's not as hard as you might think, I could show you."

"No way! I could break my legs!"

"Then I'll catch you!"

They were interrupted by John entering the room, "Hey, Dean-" He paused and looked between the two and shot a glare at Dean. He crossed his arms, waiting for the explanation.

"Hi, dad! You saw Jo come in just now, right? Anyhow, she was just dropping off-"

"How stupid do you think I am, son? I know exactly what she was doing here!"

"Nothing happened, I swear! We just watched a couple movies, just ask Sam! He was there!"

John sighed heavily, turning to Jo, "Does Ellen know about this?"

"No... but please, if you just don't tell her I promise it'll never happen again! I'm starting to warm her up to him and if she finds out about this she'll never let me see him again." Jo pleaded, getting misty-eyed.

"Dad, please.. you of all people should understand, once I lose Ellen's trust I can never gain it back. I know what I did was wrong and disrespectful. I didn't even consider the consequences when I suggested it, and after today, that will never happen again, believe me. Jo means too much to me, I don't know what I would do without her."

John crossed his arms firmly, and took a deep inhale, processing it for a moment.

"Okay.. but I swear, Dean, you're walking on very thin ice."

"Thank you.. you won't regret it."

"I hope not. Come on, Jo, I'll drive you home."

When John returned home, Dean and Sam sat together on the couch; arguing over what to watch.

"Sammy, could you go in your room for a few minutes? I need to talk to your brother."

"Ooooohhh someone's in trouble." Sam said, sing-songy.

"Now, Sam." John instructed, and he hurried up the stairs.

John sat down on a chair diagonal from the couch. He intertwined his hands; his elbows rested on his legs, and sat with a stern stare at his son.

"Is this the first time you've brought her here without me knowing?"

"Yes, sir."

"Have you ever been over to her house without Ellen knowing?"

Dean stayed silent for a moment, staring at his fidgeting fingers, wishing he'd asked any other question.

"...No."

"Dean, look at me." Dean reluctantly did as he was told, "Tell me the truth."

He took a long inhale and sighed, "Yes..."

"How long has this been going on?"

"Four months.."

John exhaled, rubbing the nape of his neck. He chuckled, "I gotta hand it to you, son, that's kind of impressive."

Dean smirked to himself, and his father continued.

"Look, I'm not mad at the fact that you're dating Jo, I think it's great. You two have always gotten along so well, I was rooting for you guys to get together, eventually. Your mother did, too... but I am mad that you've been sneaking around and lying to me this whole time."

Dean turned his focus back to his hands, a pit starting to grow in his stomach. "I know.. I just didn't want Ellen to find out, I thought you would tell her."

"I know, son, but it has to stop. You can keep dating Jo, but you can't keep tiptoeing behind Ellen's back in her own home. You've been damn lucky so far but it won't last forever. Promise me it won't happen again." John's gaze pleading him.

"I promise." Relief washed over Dean; he'd imagined this conversation in his head about a hundred times, and never did he expect his father to not only forgive but to also stay silent about their relationship.

They sat quietly for a minute or two - they weren't keeping an eye on the time - when John piped up again.

"You really like her, huh?"

"Yeah.. I do." A small smile spread across his face.

John smiled as well, "I'm happy for you. She likes you a whole lot, too."

His slight smile turned into a full grin at the remark, and he was glad Sam was no longer in the room and couldn't tease him. "Thanks, dad."

"So, uh.. you're being safe, right?"

Dean furrowed his brows, "What?"

"You know.. wearing a condom?"

"Oh, god.. um.. we haven't done anything but uh - y-yeah I will." He stuttered out.

"Good.. I'm not ready for grandkids yet."

They both chuckled uneasily, hoping the other would bring up a different subject to talk about.

As if on cue, Sam called from the top of the stairs, "Can I come down yet?"

"Yeah!" John called back, and Sam ran down to join Dean back on the couch.

"So how grounded is he?" Sam laughed and got a sharp elbow in his side.

"Shut up. Asshole.."

"Language." John warned.

"I wouldn't have to call him that if he wasn't being such an asshole..." He mumbled.

"Knock it off, Dean."

Sam giggled at his brother being scolded.

"You're not off the hook either, Sam. You knew about this, didn't you?"

"It's not his fault, I told him not to say anything." Dean defended.

"He still made the choice, Dean. You don't have to stand up for him."

Sam groaned, "That's not fair! He's the one that's been sneaking out and breaking the rules!"

"But you knew and didn't tell me it was going on. Which is just as bad."

"How?? I didn't do anything!"

"Don't argue with me, Sam. You're grounded for two weeks."

He exhaled heavily, stamping his feet as he headed up the stairs.

Dean felt a tightness in his chest; he wished he'd never told Sam. He made his way up the stairs, hoping to reconcile him.

He gently opened his bedroom door, only stepping one foot inside, "Hey, Sammy? Can I talk to you for a sec?"

"Go away." He replied, lying on his bed facing towards the window.

"Sam.." Dean sighed, shutting the door behind himself before sitting on the edge of the bed, "I'm really sorry you got in trouble."

"No, you're not. You're just going to keep doing the same crap until you get in trouble again and I do too because I was trying to be a good brother and cover for you."

Dean took a long inhale, absorbing the words. He rubbed the nape of his neck, staring at an invisible spot on the floor. "You're right.. I haven't been a good brother to you. It wasn't fair of me to put you in that position. I swear, though, I'm going to be better."

"Yeah, whatever.. Can you just go away please?"

He sighed, and returned downstairs, deciding to see what he could throw together for breakfast. Though, with everything went on this morning, he wasn't very hungry.

Meanwhile, Jo stepped inside her home, greeted by her mother, brows furrowed in confusion.

"What are you doing home so early? It's not even ten thirty. Did you and Ashley get in a fight?"

"No, no, I just wanted to spend the weekend with you." She smiled, and her mother pulled her in for a tight hug.

"You're such a sweetheart.. What did I do to deserve you?"

The words reminded her of the night before with Dean, and her heart sunk deep into her stomach. Oh god, she wished she hadn't agreed to the idea. Dean was already in enough trouble with his grades and who knows how long he'll be grounded for this.

"Is everything okay, honey?" Ellen asked.

Jo was pulled from her thoughts and realized she'd unconsciously holding onto her firmly as the guilt washed over her.

"Yeah, I'm fine.. sorry..." She let go, taking a step back.

"Jo.. tell me."

Jo exhaled, "Have you ever done something that got a friend in a lot of trouble?"

Ellen stared pleadingly at her daughter, resting a hand on her shoulder, and Jo continued.

"I just.. I feel bad that they're being punished and I'm not..." She looked towards the floor, her right hand absently caressing her left bicep.

"Well.. then you should probably own up to whatever it is you did."

"I can't.."

"Why not?"

Jo pulled her bottom lip between her teeth as if to keep the truth from escaping. She wished it were that easy; to just confess to what she did, receive punishment, and everything go back to normal. The reality, however, was much more harsh. If her mother found out that she spent the night at Dean's house, in Dean's bed, without a parent present - oh, she would be livid. She would never be able to see him again. Not even including telling her about the party, or hell, half the stuff they've been doing the last four months.

Jo took in a deep breath, shaking the thoughts out of her head, "It's too late." Which wasn't a complete lie, it was too late. In order to tell her mother about last night, she would have to confess to the entire relationship.

"Oh.. then all you can do is learn from this and try not to make the same mistake next time." Ellen said, smiling softly.

Though the smile she mustered back was fake, the advice did help her cope with the situation.

Later, at the Winchester household, the boys were setting the table as John prepared dinner.

When they all sat down for their meal, John spoke up, "So.. I was going to tell you two when I got home, but this morning didn't quite go as planned." He chuckled uneasily before clearing his throat, "Anyway.. so uh, I wasn't exactly visiting a friend yesterday."

Sam furrowed his brows at him and Dean raised an eyebrow curiously before he continued.

"I was actually visiting my girlfriend.. it's been going well for awhile, so I invited her over for dinner tomorrow so she can meet you guys."

Sam flashed a smirk at him, "That's great. Congrats, Dad."

He smiled back, "Thanks, Sammy."

John then stared expectantly at Dean, trying to gauge a reaction from him.

"That's cool.." Dean stated flatly, and started eating, his eyes seemingly glued to his plate.

"She's really great, I think you guys will get along with her really well."

"What's her name?" Sam asked.

"Nicole." John smiled.

"What is she like?"

"She likes books, and dogs, and loves kids - she's very excited to meet you two."

After a moment, John remarked, "You've been awfully quiet, Dean.."

He shrugged, "I don't have anything to say."

"Well, why is that?"

"I don't know." Dean replied, his tone, however, suggested that he wasn't saying everything he wanted to, "Sam took all the good icebreaker questions so..."

A couple minutes of silence went by before Dean felt the need to fill it, "So, how old is she?"

"Thirty five."

"Oh.. so she's like.. six years younger than you?"

John nodded, "I know that seems like a lot to you now, I mean that's like a third of your lifetime, almost. But once you get to be our age it doesn't really matter."

"Yeah, I get it.. I'm glad you're happy, dad."

John smiled, "Thanks.. I am too."

After dinner, the boys cleared the table while John worked on paperwork in his bedroom.

"So why were you so weird about dad's girlfriend?" Sam asked, handing Dean a plate for him to wash.

He took the plate, squirting a squiggle pattern of soap onto it before he started scrubbing. "I wasn't being weird.."

"Yeah, you were. It was super obvious. So what's up?"

Dean sighed, pausing for a moment before he continued washing the dishes. "It's just... I don't know. When was the last time dad introduced us to a girlfriend? Remember what's-her-face who called the house when he wasn't home and found out he had kids?"

"So? That just means he's really serious about her, right?"

"Yeah, that's what I'm worried about.."

"Why? I mean.. if it goes well we could have a mom."

Dean's heart sunk at the thought. He then rinsed the plates and placed them on the rack to dry before heading down the hall, making a beeline to the stairs.

"Dean, wait!" Sam hurried to catch up with him, "What's wrong?"

He spun around to face him, "I don't want another mom, Sam. I don't want to just forget about her and replace her like a dead dog."

"Well I never knew her! This is the only chance I have of having a mom!" Sam wiped the tears from his cheeks with his forearm.

Dean pulled his brother in for a hug, holding him tightly with one hand cupping the back of his head, the other between his shoulderblades. Sam held onto him tightly, and Dean started to feel the moisture soak through his t-shirt.

"I'm sorry, Sammy.. you're right. You deserve that. I promise, I won't do anything to stand in the way of that, okay?" He reassured, looking down at him.

Sam didn't look back, instead just nodded against his brother's shoulder.


	6. Nicole

**Summary for the Chapter:**

> John introduces the boys to his girlfriend, Nicole, over a good ol' awkward family dinner. Dean struggles with the fact that she may be around for awhile.

**Notes for the Chapter:**

> Hey, guys!! Please let me know what you think!!

The following morning, the harsh beep of his alarm clock woke him at 8am sharp. Without opening his eyes Dean lazily reached his arm over, feeling around his nightstand for the alarm. He flicked the switch off, and rubbed the sleep from his eyes before getting up out of bed.

He crossed the hall and knocked on his brother's door, "Rise and shine, Sammy!"

. . .

Dean stepped inside, "Come on, dude, it's time to get up."

Sam groaned, pulling his comforter over his head.

"Do I have to do this the hard way?"

. . .

"Suit yourself." Dean said, strolling in. He grasped the sheets and pulled them off Sam. He then slid his arm underneath him, and threw him over his shoulder, heading out of the room and downstairs.

"You're such a dick!" Sam yelled, swuirming and punching his brother's chest.

"Language, Sammy!" John scolded from the kitchen table.

Dean stopped and let go so Sam could get down. He huffed as he went into the kitchen, Dean following behind.

"Everything alright, boys?"

"Yeah, Sammy just needed a little help getting out of bed." Dean smirked, which granted him a punch in the arm from his little brother.

"Sam, quit it." John instructed.

"He started it!" He argued, pointing a finger at Dean, "He carried me on his shoulder out of bed!"

John sighed, "That's enough, I don't care what started it but I'm not tolerating it. And you two better behave when Nicole gets here." He shot a warning look between the two of them but his eyes stayed on Dean's, "I mean it."

They both nodded, and Sam sat at the table across from John, while Dean poured cereal for him and his brother.

A knot grew in Dean's chest when he was reminded that she would be coming tonight. Oh god, why did it have to be tonight?  
He took in a deep breath, running a hand through his disheveled hair, and exhaling as he shook the thoughts away.

John took a long sip of coffee, "So, this house needs to be immaculate by the time she gets here."

"Mhm." Dean said, muching on his cereal.

"The kitchen needs cleaning, floors vacuumed, bathrooms cleaned, everything dusted-"

"Oh, yes, definitely. Most break-ups are dust related."

John shot Dean an unamused look and continued on with his list.

After clearing the table, the three went their separate ways and began working.

Dean went on auto-pilot most of the day while he did his various chores, music blaring in his headphones. By the time he finished, the clock read 5:35. Nicole scheduled to arrive at six o'clock sharp.

"Alright, the two of you get showered and put on something nice. Not a suit and tie or anything, but something respectable."

"I call it first!" Sam shouted as he ran for the stairs.

"Not if I get there first!" Dean said, following close behind him.

As Sam grasped the stair railing, Dean shoved him backwards as he raced up the stairs past him.

"Jerk!" He yelled at his elder brother, getting a laugh back as a reply. Sam tackled him as soon as he caught up.

Dean arched forward, stumbling from the weight before he regained his balance.

"Ugh, get off me!" He said, prying his brother's arms off of him.

Sam made a break for the bathroom as soon as his feet hit the floor. Dean tried to stop him, but Sam dodged any attempt he made and slipped into the bathroom, slamming the door and locking it behind him.

"Ha!" Sam yelled triumphantly from behind the door, "You'll take way too long anyway!"

"No I won't!"

"Yea-huh! You take like an hour and HALF of that is just combing your hair!"

"That's not-" He sighed, cutting off his own sentence, "Whatever, just hurry up!"

Dean slumped against the wall for the next ten minutes or so, when Sam emerged.

"All yours." He said, heading down the hall to his bedroom.

After his shower, Dean went into his room and began rifling through his closet. "Ugh," he thought, grimacing at the selection. What exactly qualifies as "respectable" that isn't a suit was beyond him. As long as it wasn't ripped or dirty, it must be fine. He grabbed a blue and green flannel and a pair of jeans - the only pair that weren't torn.

Dean buttoned up the flannel and rolled the sleeves to his elbows before returning downstairs. He then sauntered down the hallway to the dining room.

"Good, you're here." John said, "Your brother set the table, could you grab some glasses?"

"Yeah."

Dean did as he was told, and placed four glasses on the table, just above the silverware. It felt weird, setting for an extra person. Not that he never had, like when a family member or friend came over, but this was different. This was a commitment. He might have to get used to this, he thought. The idea made his stomach churn.

As if on cue, the doorbell rang.

The boys trailed close behind their father, mimicking shy children hiding behind their parent in front of a stranger.

"Hi! Right on time!" John greeted, pulling Nicole in for an embrace.

Nicole smiled at the boys over his shoulder, drawing herself away, "So, you must be the Dean and Sam I've been hearing so much about."

She shook the boys hands respectively, "Ooh nice firm handshakes, your father certainly taught you well."

John smiled and they all headed into the dining room, where John served the meal.

"So, Dean, your father tells me you have a girlfriend.." She flashed him a cheeky smirk, "What's she like?"

Dean felt a heated rush to his face. He rubbed the back of his neck bashfully, smiling unconciously at the mention of her. "Um... I don't know.."

"Did he also tell you that Dean- Ow!" Sam was interrupted by a sharp kick from his elder brother.

"Shut up!" Dean said under his breath.

"Dean, don't kick your brother!" John scolded.

"I didn't kick him!"

"Yes you did!" Sam countered.

Nicole couldn't help but snicker at the textbook sibling conflict, "Be nice."

John piped up, continuing the conversation, "He's just being shy. She's a really nice girl, though. They've been friends since they were in Pampers." He chuckled, "Partners in crime, actually. When they were real little, Dean would act as a stepstool on all fours while Jo raided the cookie jar."

Nicole laughed, and Dean joined her. He saved the story as a mental note to tell Jo the next day at school.

"I guess some things never change, huh?" John smirked, and shot an acknowledging look at Dean.

Nicole eyed inquistively between the two, "Oh? I sense another story."

"Let's just say I didn't find out about them until yesterday.." John said.

"Oh. Ohh. They weren't.. you know...?"

"No no no no. Or - Well not that I know of-"

"No!" Dean corrected, the warmth in his cheeks could fry an egg, and was definitely noticeable.

"Yeah, I already asked." Sam said with a mouthful of food.

Dean buried his face in his hands, "Can we please talk about something else?"

"Sorry.." Nicole said, "So, Sam, what's new with you?"

He shrugged, "Ummm... Oh!" His face lit up as the thought came to him, "My friend's dog is having puppies soon, he said I could have first pick! So, dad.. I've been meaning to ask..."

"No." John replied.

"But I'd take care of it! You wouldn't have to do any of the work!"

"No, Sam. A puppy is way too much responsibility for a boy your age. Maybe when you're a bit older."

Sam sighed, bowing his head and focused on his plate.

"You know, Sam.. I have a dog, and he could use someone to watch and play with him while I'm at work. I could drop him off a few times a week." Nicole suggested with an empathetic smile.

"Really??" He beamed, then turned to his father, "Can she dad?? Please??"

John pulled his bottom lip between his teeth, pondering it for a moment.

"Okay. But he's your full responsibility, Sam."

Sam thanked his father profusely before him and Nicole continued on and on about dogs, and Dean's thoughts drifted and tuned it out, focusing on finishing his dinner.

After their conversation, John piped up, "So, boys... I didn't want to do it unless dinner went well, and since we're all getting along what do you think about Nicole staying the night?"

Sam smiled widely, "That'd be awesome!" He turned to her, "Wanna see my room?"

She smiled back, "I'd love to! After dinner."

John paused for a moment, "Dean?"

"Hm?" He asked, feigning ignorance to give himself a moment to come up with a response.

"Would that be okay with you, too?"

"Yeah, I- yeah that's fine." Was the best reply he could muster towards it. He showed a polite smile before turning his attention back to his, now empty, plate.

Dean fiddled with his thumbs under the table as he waited for the others to finish eating so he - hopefully - could retreat upstairs.

They soon did, and Dean made sure to gather their plates and rinse them in the sink.

Sam grabbed Nicole's hand as soon as she stood from the table, "Come see my room!" He enthused before running up the stairs.

Dean then made a beeline for the stairwell himself, before his father stopped him, "Where are you going?"

"To my room.. They're probably gonna be awhile. Sam can talk your ear off once he gets going."

"Absolutely not. You're staying down here, and you will make conversation with her. You've been ignoring her all night and I won't stand for any more of it. Do you understand me?"

Dean swallowed his frustration in a deep inhale, which felt akin to swallowing a horse pill.

"Yes, sir."

He moved to the living room, and sat at the chair diagonal from the couch. The knot in his chest was like barbed wire. Why was he so nervous? Why was this so difficult? Sam was getting along swimmingly with her, and yet Dean couldn't even manage to say much of anything at all.

When they returned downstairs, Nicole leaned in the door frame of the room, "So, Dean, when do I get to see your room? If you don't mind, of course." She smiled, "I know when I was your age I hated anyone being in there. Plus it was always a mess."

He chuckled, standing from his seat, "Yeah, I don't mind. I'll show you."

When they entered his room, Dean stood next to the doorway, unsure of how the situation was supposed to be. Giving her a tour and showing her every single item in his bedroom was a bit out of his age range, but standing back while she wandered felt just as strange.

Nicole took a few steps, and stopped at his nightstand. She eyed the photo sitting there, and turned to Dean, "Is it okay if I..?" She pointed towards the picture.

He nodded in reply, "That's fine."

She looked closely at it, and a wide smile spread across her face, "This is you, right?"

"Mhm."

"You were adorable! And your mother was gorgeous..." She trailed off, and set the picture down.

"You two were really close, huh?"

A pit grew in his stomach at the mention of her. "Yeah.."

"I'm so sorry about what happened..."

Dean shrugged and turned his focus to his feet. Maybe it wasn't the best response, but what other alternatives were there? 'It's okay'? It wasn't, nothing about it was.

A heavy silence fell between them, and Nicole felt the need to fill it, so she began looking around to find inspiration.

The milk crate caught her eye, and she started flipping through his records. "Oh, wow, you've got an awesome taste."

He smirked, looking over at her, "Thanks."

She turned to face him, "Do you play anything?"

"I can play guitar."

"Oooh, well I'm sure that was a real hit with your girlfriend, huh?"

"I've actually never played in front of her.."

"Really? You should, I'm sure she'd love it. Lemme tell you, girls love a guy who can play guitar. It's very attractive."

A rush of heat ran to his cheeks. He rubbed the nape of his neck bashfully and looked upwards at her, "You think so?"

"Mhm." She leaned against the desk, "What else are you good at?"

Dean slid his hands into his pockets and shrugged his shoulders, looking towards the floor.

"Oh, come on, I'm sure you're good at lots of things."

"Nothing I can't get in trouble for." He chuckled.

She laughed, "Well, that's still something."

Sam came inside, stepping past Dean, "What movies do you have in here?" And started rummaging through his brother's closet.

"Thanks for knocking." Dean rolled his eyes and pulled the box of movies out.

"Why? Do you have another secret girlfriend hidden somewhere?"

"Shut up, at least I can talk to a girl."

Nicole interjected, "Boys, settle down."

"Obviously you're not doing it right, 'cause they don't stick around very long." Sam retorted.

"Screw you!"

"That's enough!" Nicole interrupted, effectively quieting them, "Now both of you apologize to each other."

"I'm not apologizing to him, he's the one that just barged in here and started being an asshole!" Dean argued.

"I don't care! Sam, go to your room. Dean, you stay in your room. I'm going downstairs, and I don't want to see either one of you until you've both apologized." She gave them both a stern look before exiting the room.

Sam huffed, "I'll be waiting in my room." He said as he walked across the hall.

"Don't hold your breath." Dean said before shutting his door behind him.

He laid in bed, staring at an invisible spot on the ceiling for a good five, maybe six minutes before his father came in.

John let out a long sigh and sat on the edge of his bed. Dean pushed himself up so his back was against the headboard and he was eye-level with his father.

He turned to face his son, "What is it with you and your brother? Why do you always have to bicker with him?"

Dean opened his mouth to speak but John decided it was best to continue so he wouldn't have to hear an excuse, "Dean.. you're the oldest and it's your job to be the bigger man. Always. Even if he pushes your buttons, you have to be mature and not let it get a rise out of you. Now go apologize."

Dean sighed, but he knew his father was right.

He knocked twice on Sam's door before stepping inside, "Hey, Sam.. I'm sorry about earlier."

Sam stared at him, eyebrows high, "Who are you and what have you done with my brother?"

Dean had to stop himself from rolling his eyes, "Don't gloat, let's just go downstairs."

"But I didn't apologize to you."

Dean held his arms out wide before dropping them back to his sides, "Well, let's hear it."

Sam took a deep breath, "I'm sorry.. I took it too far."

"It's okay. Let's go."

Sam smiled and followed his big brother down the stairs.

"So, are you guys friends again?" Nicole asked.

"For now." Sam said with a laugh, and got a laugh from Dean as well.

The rest of the night was mundane, and for them a normal, boring family night was a very good thing. Dean, however, fell asleep on the couch soon after the movie started.

**Notes for the Chapter:**

> If you have a favorite part or any suggestions, leave me a comment! I'll read and reply to all!


	7. Third Chance is the Charm

**Summary for the Chapter:**

> Jo finally tells her mother about her relationship with Dean.

He awoke in the morning sprawled across the couch with a pillow under his head, and a blanket on top of him. He must've fallen asleep, he thought. Dean rubbed the sleep from his eyes and rolled off the couch, catching himself with his hands before pushing himself up and on his feet.

The school day started as any other, until Dean and Jo met in their shared Biology class.

As Mrs. Stillman went on with her lecture, Dean felt as if she'd been ranting for hours. She was old; definitely past mid-sixties. Every word that came out of her sounded as if it'd died in there, so monotone and lifeless.

He let out a sigh and leaned over to Jo, sitting in the desk beside him, "I think I'm in the wrong class. I'm supposed to be in Biology, not Falling Asleep 101."

She hid her giggle with her hand, "Shhh."

Mrs. Stillman swung around from what she was writing on the board, "Is something funny, Joanna?"

Dean couldn't help but chuckle, while Jo's heart raced, "No, ma'am.. Sorry..." She buried her face in her notes and kicked Dean's leg as soon as Mrs. Stillman turned around.

That didn't discourage him, however, as when she'd started talking about the human reproductive organs, Dean leaned over once again, "I think in order to teach about sex you have to have had it in less than fifty years."

Jo couldn't help but chortle - a little louder than she would've liked - and got the attention of the whole classroom giving her inquisitive looks.

"Ms. Harvelle, if you interrupt one more time I'm sending you to the principal's office, do you understand me?" Mrs. Stillman said in a stern tone - the only emotion her voice could convey.

"I understand, ma'am. Won't happen again. Sorry..."

Jo wasn't used to being the noisy one in class, unlike a certain boyfriend of hers, the thought of going to the principal's office made her heart sink into her stomach.

The glare she gave Dean warned him not to get her in trouble again. Although he did find it funny when she got scolded, he didn't want her to get into any real trouble, so he remained silent for the rest of the class.

After the bell rung Jo pulled Dean aside in the hall and gave him a hard punch in the arm, "Thanks for getting me in trouble, jerk."

He winced and held his hand against the spot, "Hey, it's not my fault you think I'm hilarious."

He wore that damn charming smirk and Jo just couldn't stay mad at him. He was kind of right, too. Not that she'd tell him, though, she was too stubborn.

"Whatever.. What do you have after this?" She said instead.

"Math. But I was thinking we could ditch instead."

Jo quirked an eyebrow at him, "Yeah, we should. Being grounded three times in one week would break a record."

Dean scoffed, "This ain't my first rodeo. It'll be fine, trust me."

"Hmm... What happened last time you said that? Remind me."

He sighed at his failing to convince her, "Okay, yeah, the overnight thing was my bad, but no one found out about the party. And no one's going to find out about this. I promise."

Jo let out a sharp exhale, "What's your plan?"

"Calling in a fake call saying there's a family emergency and you need to go."

"And for you?"

"Going home sick."

Jo rubbed the back of her neck, "What exactly would we be doing once we left?"

Dean shrugged, "I dunno.. Go see a movie, walk in the park, whatever."

"And.. why can't we do that after school?"

He flashed her a smirk, "It's more fun this way."

"No. No, you're already in too much trouble. I'm trying to coax my mom into liking you, and that's never going to happen if you keep up like this."

Dean was stunned to silence for a moment t her honesty. He pulled his bottom lip between his teeth while he processed it, "You're right.."

"Look.. I know you just want to spend time with me and I want to too..." She sighed, "Tonight I'll tell my mom you asked me out, and then we can just act like we're starting from the beginning."

"Seriously?" He smiled, which quickly faded as the reality ocurred to him, "Are you sure now is a good time? She already doesn't like me. A study partner is one thing, but boyfriend demonizes me in more ways than one. I mean, suddenly I'm the guy who could break your heart or get you pregnant."

Jo felt flustered at the thought of the latter, but quickly shook it out of her head.

"She might be upset at first, but I know she'll change her mind after she gets to know you."

He chuckled, "Yeah, she will. She'll hate me more."

"Stop it, she'll love you."

Dean shrugged in disbelief, "Alright.. So what exactly are you going to say?"

"I'm going to tell her the real story."

Jo then thought back to that day.

She had stayed after school for a debate team meeting. Her mother insisted she join a club and arguing is one of her better qualities, so debate was the best of a bad situation.

Jo hadn't counted on rain that afternoon, and was soaked the minute she stepped outside. Dean knew she had a club meeting today, and about the storm, so he'd been waiting for her with an umbrella. He rushed over and handed it over while he shrugged his leather jacket off and draped it over her shoulders.

The raindrops peppered her face and hung onto every eyelash and Dean was noticably staring. In a blink of an eye, he'd leaned down and closed the distance between them. He kissed her with urgency, and Jo could feel him smile when she kissed him back. His lips against hers felt better than she ever imagined. Feeling the heat of his skin brushing against her frigid lips sent a shiver down her spine. She placed a hand on the nape of his neck, pressing him closer to her.

Jo pulled away for air and Dean didn't skip a beat before asking, "Will you go out with me?"

"Took you long enough." She teased. They shared a smile before he joined her lips again.

Ellen's silence afterwards was worse than anything Jo imagined she'd say.

"So...?" Jo finally said. Her heart was performing a drum solo at the suspense.

Ellen sighed, "You know how I feel, Jo."

"Yeah, you said to be careful, and I am. He asked me on a date, not go rob a bank."

"That's not what I want you to be careful about."

"Oh my god, it's a first date. I don't think that's going to be a problem."

"I'm just saying that it's easy to get lost in a moment and get taken advantage of."

"Okay, thanks. Good talk." She exhaled exasperatedly as she made a beeline for the stairs.

"Don't be like that, Jo. I just don't want you to get hurt."

Jo spun around on her heels, "The only person hurting me is you!"

Ellen furrowed her brows, taken aback. Before she had the chance to reply, Jo continued.

"He's my best friend and I can't even talk about him without you dumping a bunch of bullshit accusations about him on me! Would it kill you to try to be supportive for once? God, if literally anyone else asked me out you would've been just as excited than I am and asking a million questions, but no, because it's Dean you have to give me this big lecture like I'm about to star in a Lifetime movie."

"That's enough, Jo," Her mother asserted, "I'm just trying to look out for you."

Her voice then turned softer, "He's been there for me ever since dad died. Through everything. He's even there with an umbrella when it rains because God forbid I experience any discomfort. That's the real him. I know he doesn't always make the best choices, but he's a good person."

Ellen scanned her daughter's features, a knot grew in her stomach at the tears streaming down Jo's indignant expression.

She pulled her in a tight embrace, "I'm sorry, Jo... I haven't been fair to you or to him." She pulled away and wiped the tears from her cheeks, "Why don't you invite him over for dinner? Then we can get to know each other formally."

Jo was in the middle of turning the padlock on her locker when she was approached.

"Hey." Jo turned to see a girl who looked vaguely familiar, probably on the cheer squad or something. "So... I saw you with Dean Winchester at the party on Friday. Are you two like, a thing now?"

"Yeah.." Jo replied, anxious to find out where she was going with this.

"Don't get me wrong, I get why. He's gorgeous, he breaks the rules, and he knows exactly what to say to make you melt... I mean, I know you guys are friends but I'm sure you know about his track record with girls."

Jo sighed exasperatedly before slamming her locker shut. She spun around to face the girl, "How is this any of your business? I don't even know you."

"It's my business because I used to be in your shoes, and I'm trying to save you from heartbreak. And my name is Amber, by the way."

"Well it's nice to meet you, Amber, but I've already heard the 'you're making a big mistake' speech twice, so I'll save you the trouble. I gotta go."

As if on cue, Dean's voice greeted her from behind, "Hey!" His smile stiffened when he saw who she was accompanied by, "So, I didn't know you two knew each other... Amber, how've you been?"

"Great, actually." She smiled coyly, "I'm sure he already told you, but I started seeing your friend Jake."

"Oh.. he didn't, actually..." Their was clear apprehension in his voice, "That's great, I'm happy for you two."

"Hm," She tisked, "Well, I gotta go. Nice talking to you, Jo."

Jo stepped towards him after she'd walked away, "So... that was weird, huh?"

"Yeah... sorry about that, we kinda dated awhile ago.. it didn't end well."

"I know, she told me.. but what happened? She was vague on the details, she just basically told me you were a jerk."

Dean sighed, pulling his bottom lip between his teeth as the memory returned, "Um.. well, yeah, I was. I don't really wanna get into it, but yeah..."

"Oh..." Jo paused for a moment, not sure of what to say.

"Look, Jo.. I was an idiot, okay? I'm not like that anymore."

"Well, that's not completely true... You're still an idiot." She smiled.

He laughed, mostly out of relief.

"So, anyway..." Jo changed the subject, "I have good news."

"Yeah?" Dean stared expectantly.

As hard as she tried to hide it, a wide smile spread across her face, "My mom wants to get to know my new boyfriend over dinner."

"Seriously?" He beamed, "When?"

"How about tonight?"

"Yeah, tonight's great!"

Jo stood on her tippy-toes and gave him a quick kiss, "It's a date." She slung her backpack over her shoulders and made her way out the front doors.

Dean had retied his tie probably twelve times by now, but whatever he did it felt like it was suffocating him. Granted, maybe some of that was due to his anxiety about the night. Some of it was because he hated ties, but this was a special occasion, and he had no choice but to compromise his comfort.

"How long does it take to tie a tie?" Sam criticised from the doorway.

"Shut up.... does it look okay?"

"It looks good. What time is dinner?"

Dean pulled up his left sleeve to check his watch, only to find his bare arm there. "What time is it?"

"5:30."

"Shit. I gotta go." He said before rushing down the stairs and out the door.


	8. Meet the Parent

**Summary for the Chapter:**

> Dean has dinner at the Harvelle's so Ellen can get to know him formally, as her "new" boyfriend.

Dean took in a deep breath as he approached the Harvelle's house. Each step was labored; the closer he got, the heavier his feet felt. After what felt like hours, he reached the front door.

He froze for a few seconds after the door opened, looking over Jo. She wore a burgundy a-line dress with a pleated skirt that was a couple inches above her knee. His eyes traced along her shoulders to where the dress ended, at a loss for words.

His eyes quickly shot up to meet hers when he'd realized he hadn't said a word yet, "You... you look amazing."

Jo smiled, "Thank you... you look very handsome. I didn't know you owned a suit," She joked.

"I didn't know you owned a dress." He countered, making them both laugh.

Jo then gestured him inside, and Dean followed her into the kitchen where her mother was.

Ellen turned around as soon as she heard them approaching, a smile instantly grew on her face as she saw him, "Ooh, well don't you look handsome."

"He does, doesn't he?" Jo smiled affectionately at him and he could feel the heat rising in his cheeks.

"Why don't you help me set the table?" Jo suggested, handing Dean the silverware and napkins while she carried the plates and glasses.

Jo paused arranging the flatware, amused by Dean delicately folding the napkins around the cutlery.

"Where'd you learn to do that?"

"My mom." He stated, never stopping his task, "I learned before I could even see above the table."

"Aww... You're doing great, by the way." Jo locked eyes with him, smiling softly.

"Thanks... but it's early," he laughed.

Jo giggled, "You'll be fine."

Ellen interrupted their conversation as she carried in the meal, "Dinner's ready." She sat at the end of the table, Jo on the right, and Dean across from her on the left.

"So, Dean... tell me about yourself."

He was caught off guard by the question, "I don't think there's much to say.."

Jo gave him an incredulous look, "Don't be modest."

"Um...." He paused, thinking for a moment, "I like cars. I like fixing them, I think I'm pretty good at it. It's really cool, if one part stops working the whole thing stops, so you have to figure out which part is busted. It's like a puzzle," He smiled.

"That's really cool. You know, it takes a sharp mind to do something like that. Don't waste it."

"Yes ma'am."

"Speaking of... how are your grades doing?"

"Better, I think...." Dean surmised.

"Good.. I hope Jo being your tutor won't distract you from studying."

"I can't make any promises..."

He and Jo shared a laugh, while Ellen just gave him a warning glare.

Dean cleared his throat, "It won't be a problem."

Ellen nodded, "So.. how's Sam?" She quickly changed the subject, "I haven't seen him since he could barely walk."

"He's good. He can walk just fine now." He joked, eliciting a laugh from Ellen. "He's a good kid, though. Maybe he can come over one day."

"I'd like that."

The rest of the dinner was quiet, though a good quiet. A comfortable quiet.

Ellen began gathering the plates from the table when Dean stopped her, grabbing the dishes from her arms, "I got it." He said with a smile before sauntering into the kitchen.

She smirked, impressed with him.

Jo smiled widely at her mother, "See?"

"Why don't you go dry the dishes for him, hm?" She replied, avoiding admitting that she might be wrong.

Jo did as she told, and dried the dishes as Dean finished washing them.

"Thanks for doing the dishes." Jo commented, "Mom was impressed."

A smile grew across his face, "Really? It's not a big deal..."

"No, but the gesture counts. She really liked that." Jo planted a soft kiss on his cheek, and she could feel him smiling again.

Ellen couldn't help but crack a grin watching them in the doorway. Jo caught her mother in the corner of her eye as she pulled away from him, "Hey, mom."

"Dean, do you have to be home by a certain time?"

He turned around as he dried his hands off on his jeans, "No, my dad's working overnight tonight."

"Oh, good. I was thinking we could all watch a movie."

"Yeah, that'd be great!" He beamed, though he tried to downplay his excitement.

Jo smiled at her mother, who gave her a knowing look.

Ellen sat on one end when the movie began, Jo taking the other end before Dean got the chance, forcing him to sit in the middle.

He sat down and faced a dilemma. Normally, he'd sit on the end and have one arm on the arm of the couch and the other at his side. Placing his hands at his sides would have him touching Jo and Ellen's thighs, and holding Jo's hand felt somewhat awkward, so he decided to keep his palms flat on his lap -which he soon found was even more awkward.

Jo sensed he was uncomfortable and slid her hand over to his, intertwining fingers and holding his hand in her lap. She leaned towards him and whispered, "Relax... just act like you would at home."

He squeezed her hand ever-so-slightly, rubbing his thumb across the back of her hand as a silent reply.

Ellen glanced at the two, smiling to herself before leaving to go make some popcorn.

Jo took the oppurtunity to kiss him, pressing her lips firm, but tender, to his.

As she pulled away she placed a hand on his cheek, staring into his eyes in a way he hadn't seen before. Her eyes were speaking a thousand words of a language he didn't understand. His lips parted barely as he stared back, trying to read her.

"I'm proud of you." She finally said, "I honestly didn't think it was possible but you changed her mind."

A grin crept upon his face, "I can't take all the credit. You convinced her to give me a chance."

She didn't reply, only kissed him again; slower this time. Savoring every touch and taste, his tongue grazing across her lower lip, touching the boundary but never crossing it. The only thing that could pull her away from this was just in the other room, and as luck would have it, was just about done and about to come back.

She pushed away from him, seating herself back to where she was, illuding as if nothing had happened, and Dean did the same.

"Did I miss anything?" Ellen asked as she handed them their bowl of popcorn before returning to her seat.

"Nope... nothing exciting." Dean lied, taking a handful of popcorn.

**Notes for the Chapter:**

> Hey, guys!! Please let me know what you think!!
> 
> If you have a favorite part or any suggestions, leave me a comment! I'll read and reply to all!


	9. Adventures in Babysitting: Part 1

**Summary for the Chapter:**

> John is going out of town but he doesn't want to leave the boys home alone again, so he decides to ask Ellen to watch them for the weekend.

"I'm glad you came tonight." Jo wrapped her arms around his neck and planted a kiss on his lips.

He wrapped his arms around her, "Thanks for having me."

"Jo?" Ellen interrupted, "Can I borrow him for a second?"

Jo sighed, knowing what was coming, "Don't let her scare you." She whispered, then kissed him on the cheek before leaving the room.

Ellen stepped closer to him, "Dean... I'm very happy that Jo convinced me to give you another chance. You're a good young man. You have your mother's heart."

Dean's heart fluttered -somewhat out of relief- and smiled, "Thanks, Ellen... that means a lot."

"Of course... but I'm not done. I like you, Jo adores you, but that does not give you immunity, okay? I still have my eye on you. Keep your grades up, stay out of trouble, and you'll be fine."

"Yes, ma'am."

He held his hand out for her to shake, and she instead pulled him in for a hug. Dean tensed at first out of surprise, but returned the hug even tighter.

"Thanks for coming. I'd love to have you again." She said, pulling out of the hug.

"Thank you for having me," He smiled.

The following morning Jo slid out of bed with a spark in her step, greeting her mother warmly in the kitchen, "Good morning, mom!"

"Well, what's got you in such a good mood?" Ellen replied.

Jo leaned over the kitchen island across from her mother, "Last night..." She smiled, staring down at her hands, "Thank you for letting him come over. What did you think?"

"He's a good boy. He's sweet." Ellen paused, "He loves you."

"How could you tell?" Jo smirked, hoping for ammunition to tease him with.

Ellen took a long sip of her coffee, smiling softly, "He looks at you the way your father used to look at me."

Her face lit up, heat rushing to her cheeks, "Really?"

"Mhm..." Ellen trailed off, losing herself in her thoughts.

The sudden phone ringing on the wall pulled her out of her thoughts. She picked it up, "Hello?"

"Hey... Ellen... it's John." His familiar gruff voice brought back a flood of memories - some unwanted.

"Hi, John... what is this about?" She said, cutting right to the chase. They hadn't spoken in over a decade.

Jo's head darted from her plate to her mother upon hearing the name.

"I um... actually have a favor to ask of you."

"Favor? You must be joking."

He let out a long sigh, "I deserve that.... Listen... I'm going out of town for the weekend and I don't want to leave the boys home alone again. And since you and Dean have been getting along I thought maybe..."

"You want me to babysit."

"Yeah.. yeah, basically. I'm sorry to ask this of you, but Dean's been kind of a handful lately, and I don't exactly trust him to have the house to himself for the weekend."

"That's fine... I get it. Bring them over whenever."

"Thank you. I'll definitely repay the favor."

"I'm counting on it." Ellen poked, "And make sure they bring their tooth brushes."

"Yes, ma'am. Thanks again."

After exchanging goodbyes, she hung up the phone.

"What was that about?" Jo asked, intrigued.

"He wants me to babysit Dean and Sam this weekend while he's out of town."

Jo chortled, "Babysit?"

"Dean apparently can't be trusted home alone, so he wants me to keep an eye on him."

"I'm sure he's thrilled about it." She laughed.

"I don't need to be babysat, dad."

"Well, your recent behavior says otherwise."

Dean huffed, "Inviting my girlfriend over to watch a movie? Is that a crime?"

"Dean, please. We both know that's not why you brought her over."

"Nothing happened! And don't act like you never did that when you were my age."

"This isn't about me!"

"So you admit it?!"

"That's enough, Dean! Look, your grades have been slipping, and you've had your run of the house every time I have to work late or leave for a couple days, and I think spending the weekend with discipline from Ellen could do you some good."

"Yeah, maybe cause she's actually home..." He mumbled, shoving clothes into his backpack.

"Excuse me?"

"Nothing." Dean replied sharply.

"Do you have any idea how hard I work for you two? I don't just get to pick and choose hours, I just have to go when I'm needed."

Dean zipped up his backpack and slung it over his shoulder, "We're gonna be late. Ellen is very punctual."

John kept a stern stare on his son for a moment, Dean mirroring him, not breaking the stare. John turned on his heels and left the room, "Sam? Are you almost ready?"

The drive over was only about five minutes, but the tension in the air was suffocating. John was waiting for an apology, though Dean didn't regret a word. This resulted in the thick silence between them.

"...Did I miss something?" Sam whispered to his older brother.

"No." He replied plainly without turning away from the window.

"Your brother is just a little upset about the situation." John chimed in.

Dean tisked, "Understatement."

"Really?" Sam furrowed his brows at his brother, "I thought you'd be over the moon about spending two whole days sleeping over at your girlfriend's house."

"Sam, I'll hardly be able to look at her with Ellen there."

"What did you want to do with her?" Sam teased with a smirk.

"That's not- I didn't mean.... shut up."

He laughed, warranting a sharp elbow in his side from his elder brother.

"Ow!" Sam yelled before retaliating with a punch to Dean's shoulder.

"Boys, that's enough." John scolded, "I don't want any of this behavior this weekend, do you understand me? Absolute best behavior."

The car slowed to a stop as they reached the Harvelle's.

"Alright, have fun. I'll call you guys tonight, okay?"

"Bye, dad!" Sam said as he slid out of his seat and made for the front door.

Dean started to slide over to Sam's open door when John got his attention, "Stay here for a second."

After reluctantly complying, John continued. "When I say 'best behavior' I don't just mean fights with your brother."

"I know, dad."

"No, listen. I know spending two days at your girlfriend's house sounds like a dream come true, and at some point you might be alone with Jo, and think it's a good idea to-"

"Dad, I get it." Dean interrupted, just wanting this conversation to end.

"I'm not done. My point is, it's easy to get lost in the moment, but if you get caught..."

"Oh my god..."

"Dean, I don't want you to lose Jo, but if you do something like that, you will. That's all I'm saying."

"Okay. I won't."

"Good.... um.. while we're on the subject, do you.... have protection? I think I have some in-"

"I'm leaving." Dean hastily slid out of his seat and shut the door.

He exhaled heavily, as if the discomfort of that conversation was trapped in his lungs. He shook the thoughts out of his head and quickly joined his brother on the porch.


	10. Adventures in Babysitting: Part 2

**Summary for the Chapter:**

> The Winchester boys get settled in at the Harvelle's.
> 
> (So it seems like this is going to be at least a 3 or 4 parter! I have plenty more to write about this chapter, but I've already hit 6k with this one and didn't want to keep anyone waiting! :D Let me know what you think!)

As if on cue, the door swung open revealing Jo, greeting them with a warm smile, "Well, if it isn't my two favorite boys."

"Ha! She called me her favorite." Sam pestered.

"Well, obviously I'm her TOP favorite." Countered Dean.

"Top pain in the ass, maybe." He snickered.

Jo chortled, holding the door open for the both of them. "Girls, you're both pretty. Come inside."

"Are you two arguing already?" Ellen said as she made her way into the entry, "Well, Jo, I owe you five dollars."

"Told ya!"

"Yeah, yeah, why don't you go show them to their room?"

Jo started up the stairs, the boys following close behind. Passing her and her mother's rooms she directed them to the guest bedroom at the end of the hallway.

"Here you are. Breakfast is at seven, activities are in the evening, and room service is available until ten pm." She jested, feigning her best customer service voice.

Dean laughed and like a flick of a light he turned on the charm with a cocky smirk, "Room service, huh? What does that include?"

Jo mirrored his expression. Her eyes noticably trailed down to his lips, pausing there for a moment before meeting Dean's eyes again.

"Eugh, I'm gonna throw up." Sam interrupted before Jo could get a word out - though anything she would've said wouldn't have been very appropriate in front of him, anyway. Or at the least just very, very, awkward.

"Sorry, Sam," Jo sheepishly apologized, "I'll meet you two downstairs."

After she was well out of earshot, Sam confronted his brother, "Do you have to do that in front of me?"

"Oh, come on, it was just a little flirting." Dean dismissed, tossing his backpack on one of the beds.

"I don't care, it's gross!" Sam scrunched his nose in disgust, "I don't want to picture you and Jo doing anything.."

"Fine, I'll try to keep it to a minimum. Let's go."

Downstairs, Ellen and Jo were sat in the living room; Ellen on the armchair opposite to the couch, where Jo was situated. Dean sat beside her in the middle, about to put his arm around her but opted on keeping it on the back of the couch due to the present company. Sam followed, joining them on the couch beside his brother.

"Now, I'm excited to have you boys here but we do need to go over the house rules." Ellen announced.

Jo leaned to whisper in Dean's ear, "Here comes the fun part." Warranting a snicker from him.

"Jo, stop distracting him."

Dean glanced an amused smirk at Jo before returning his attention to Ellen.

"Anyway... I know it's the weekend, so you guys can stay up, but I expect all of you in your own beds-" She said, looking directly at Dean, "-no later than eleven. Food and drinks are allowed upstairs, I just ask that you be careful... Oh, and breakfast is at nine."

"Okay. Sounds easy enough." Sam replied.

"Wait, so you're saying if I have a nightmare I can't crawl into bed with you in the middle of the night?" Dean joked, keeping a straight face.

Jo fought laughter but couldn't help let a giggle slip out.

"No." Ellen stared back, unamused. "Sam, could you give us a minute?"

He simply nodded and went upstairs.

"I want to make this very clear," Ellen started, her voice low and serious, "I want you all to have fun this weekend, and I'm sure you two are especially excited about spending the weekend together, but I will not tolerate any fooling around under this roof, understand?"

"Yes, ma'am." Dean assured.

Jo, a bit mortified by her mother's words quickly changed the subject, "Is that all? Can we go?"

"I'm not done. If you two are in a room together, you keep the door open or have Sam with you, alright?"

"Yes, ma'am." Dean repeated.

Ellen paused for a moment, staring at her daughter, "Jo?"

"Yes, mom..." Jo exasperatedly said, just wanting the discussion to end.

"Good. That's all, you can go."

Without skipping a beat, Jo pushed herself up off the couch and made a beeline for the stairs, Dean following close behind. Near the top of the stairs, Dean commented, "If you thought that was awkward you should've heard what my dad said to me."

"Oh, god, what did he say?"

"You know, the old 'it's easy to get lost in the moment, blah blah blah' and told me not to do anything like that with you, just like your mom said..."

"Yeah, and?"

"And then he said, 'While we're on the subject...' and asked me if I needed a condom."

"Oh my god!" Her face scrunched in a mix of surprise and disgust.

"I know."

"What are you guys talking about?" Sam asked as they reached the top of the stairs.

"Nothing." Dean deflected.

He rolled his eyes, "Whatever. What do you guys want to do?"

"I don't know... what do you wanna do?" Jo asked, quirking her eyebrows at her boyfriend beside her.

Dean turned to look at Jo. He could think of 10 things he'd like to do with her, and his mind began to wander.... Quickly, he shook the thought out of his head, "U-um... I don't know."

"You guys are so boring." Sam complained.

"Well, I don't hear you coming up with any ideas." He countered.

"Why don't we get our homework done now, so we don't have to worry about it the rest of the weekend?" Jo suggested.

"Uh, no. The way to do it is put it off, forget about it, remember it Sunday night and then cram until 1am."

She stared back at him, unamused. "Nice try. Come on, I'll help you."

He sighed, following Sam into their room. He begrudgingly grabbed his backpack and joined Jo in her room. She sat on her bed with her books laid out in front of her. She held one hand out and pat the bed, gesturing him to sit next to her.

Dean started pulling clothes out of his backpack, getting them out of the way. "What are we starting with?"

"The one you hate the most."

He groaned, "Why?"

"Because then it's out of the way and you don't have to do it later. The same reason we're doing homework now."

"Sure.. I think you just like watching me suffer."

"It'll be fine." She planted a soft kiss on his cheek and flipped open to the page they needed in her math textbook.

After they completed all their homework, Dean collapsed back in the bed with an exasperated sigh.

"Settle down, drama queen. You finished a few subjects of homework, not run a marathon."

"My brain ran a marathon."

"Well, now you're all done and we can relax."

"Mhm... c'mere."

She laid back, turning towards him and wrapping an arm around his waist, resting her head on his chest.

They laid still there for a few minutes, Dean was even beginning to drift off a little when Jo finally spoke again, "I hope you know my mom really does like you..."

He stayed silent for a few moments and Jo just decided to continue, "She's just.... having a hard time fully trusting you because... you know... your dad."

Jo felt his chest heave as he sighed, "Yeah." He didn't have anything to add- or defend, for that matter -so that was the best he could come up with.

"I don't know if I've ever said anything before, but I'm sorry... about your dad."

Her chest ached at the reminder of him. She tightened her grip around Dean's torso, pulling herself closer in the process, "I don't blame you... you had nothing to do with it."

"I know, but-"

Jo cut him off, "I don't want to talk about it..."

Dean understood. He wished desperately that he could somehow do something about it but he couldn't. He put an arm around her along her back, resting his hand on her waist. Resting his other arm on top of hers; grasping it gently in his hand, ever so often rubbing his thumb along her skin. A tiny gesture in itself, but it always comforted her coming from him.


	11. Adventures in Babysitting: Part 3

**Notes for the Chapter:**

> I'm so sorry this took so long! I hit a wall for awhile there, but I'm back! Stay tuned for even more after this! I will continue updating regularly!

Ellen then knocked on the open door before stepping in. Jo pushed herself up, wiping her eyes with the back of her wrist.

"What's wrong?" Her mother asked.

"Nothing... what did you need?"

"I was just wondering if you guys were hungry at all."

Dean was sitting upright at this point, "I could eat."

Jo nodded, "Yeah, I'm pretty hungry."

"Alright.. why don't you two go downstairs while I get lunch started?"

They complied, and headed downstairs where Sam was already sat in the living room.

"Hey, Sammy." Jo greeted, joining him on the couch, Dean sitting beside her.

"Only he can call me that." Sam said.

Dean smirked at that. He knew he didn't care much for the nickname, but it's nice that it's special.

"Fine,  _Samuel."_ Jo emphasized his name.

"Ugh, no."

"Okay. Would you prefer Samantha?"

Dean snickered, "I think that's the one." He laughed, getting a punch in the shoulder from his brother.

"Lunch is ready." Ellen called from the kitchen.

Dean took the liberty of clearing the table and carried the plates to the kitchen counter. He started to place them in the sink to rinse, when Ellen got his attention. 

"Can I ask you something?"

He turned around to face her and his heart picked up the tempo, "Yeah?"

"I just was wondering... your dad worked overnight Thursday, and now he's going out of town for the whole weekend. Does he do this a lot?"

"Yeah... yeah he does." He bowed his head and started fiddling his fingers.

Ellen fell silent. Her heart sunk seeing him like this. "Dean..."

He looked up and met her eyes.

"Are you okay? I mean.. at home?"

The question hit him like a ton of bricks. His chest twisted into a knot, and an overflow of pent-up emotions crept their way out. He turned his focus to the floor this time, "No. I mean.. things are good with Sam and me but dad......" He trailed off, the words he wanted to say glued to the tip of his tongue.

Jo entered just then, stopping in her tracks once she realized she was interrupting something. "What happened? What's wrong?"

"Nothing..." Dean dismissed, "I could use some air. Wanna come on a walk with me, Jo? Is that okay?" He turned to Ellen, asking her permission.

"Yeah, that's fine." She gave a sympathetic smile to Dean before they left the kitchen and out the door.

"So, seriously. What's wrong?" Jo asked as they got to the sidewalk. "Did she say something to you? Because I've talked to her a hundred times about-"

"No, no, she was nice, don't worry." He took a generous pause, taking in their surroundings, "Do you wanna go to the park?"

"Dean." She stopped and he turned to face her. Her arms were crossed and she was giving him a stern stare, pressing him to tell her the truth.

He sighed, "Don't look at me like that."

Jo's face didn't budge, "Talk to me."

Dean rolled his eyes, "Fine. She said that my dad worked overnight thursday and is out of town this weekend and asked if he does that a lot. And I said yes, and she asked if everything was okay at home, and then you came in."

She paused a moment, "Well... _is_ everything okay at home?"

He took a deep breath, pulling his bottom lip between his teeth, "I got in a fight with him before we came."

"About what?"

"I told him I didn't need a babysitter and he said my recent behavior said otherwise," He tisked, "And that having discipline from Ellen might do me some good.... and I mumbled, 'Yeah, maybe cause she's actually home.' And he started to go off about how hard he works for us, he doesn't get to pick hours, blah blah blah..."

"I get it... he should've apologized, not get mad at you."

"The thing is, I'm not even complaining about his job. It sucks, but he can't do anything about it. But he doesn't have to be drinking the whole time he is home, or going off every weekend to go fuck his girlfriend."

"I'm sorry..." She took his hand in hers, holding it tight.

Dean exhaled, feeling the relief of letting it all out, "I'm sorry for the language I'm just... frustrated."

She broke out into a smirk, "Since when do you care about using bad language in front of me?"

He smiled with a shrug, "I don't know, since it's my dad's sex life it felt inappropriate." He cringed as the words left his lips, scrunching his nose, "Ugh... I never want to say the words 'my dad's sex life' ever again."

Jo giggled, "Yeah, let's not talk about it again." 

He chuckled, "I don't know... his girlfriend is really nice just.. they're getting kinda serious and I'm not ready to call anyone 'mom'... like, ever."

"Yeah... I would feel the same way if my mom was dating."

"Has she ever dated anyone?" He asked and quickly corrected himself, "I-I mean if it's not crossing any boundaries..."

"If you can talk about your dad's sex life I think I can tell you if my mom has dated anyone." She laughed, gently elbowing him in the side. "No, she hasn't. That I know of, anyway. I'm not sure if she would tell me. I mean I probably wouldn't want to know, so maybe she knows that, I don't know..."

"I get it.... I'm glad we can talk about this. The only other person I have that I could talk to is Sam, and he doesn't remember mom, so it's different..."

Jo smiled at him, "I'm glad I can talk to you about it, too." 

 

They didn't talk after that, just enjoyed each other's company as the lapped around the block. 

 

"I don't wanna go inside yet." Dean said, taking a seat on the porch step.

 

Jo sat herself beside him. After a couple minutes of quiet between them, she asked, "So, how long have you had a crush on me?"

"Um.... let's just say 'a long time'." He deflected.

"Come on, how long?"

He let out a long exhale, running a hand across the nape of his neck, "Do you remember when we were five, and Iswore that I could climb that huge tree in your yard and you told me there was no way?"

"And you did it anyway. Remind me, how did that work out?

"Hey, I  _did_ climb it. But on the way down I scraped my knees, and you ran inside and got the first aid kit and patched me up."

Jo smiled as she recalled it, "That's when you started liking me? Why?"

"You're really milking this, aren't you?" Dean teased with a smirk, hoping it would get her to drop the subject.

"Tell me." She prodded, her soft stare breaking down the barriers he was trying to build.

 

"I don't know..." He lied, "I guess because it was really sweet of you... I mean, you could've just gotten your mom, but you didn't. You took care of me... and you were really gentle because you knew it hurt, and you kissed them afterwards..... Which was the first and only time I've ever been jealous of my knees."

 

Jo broke into a wide grin and pulled him into a kiss, "You like to act like a tough bad boy, but you're really just a big teddy bear."

 

He scoffed, "I am not..."

 

"Yes you are." She said sing-songy.

 

"Shut up." He defended, trying not to smile, "This is why I didn't want to tell you."

 

 

* * *

 

"So, Sam... do you like anyone at school?" Ellen asked the boy.

 

He paused, fighting the smile at the question, "Kinda... this girl in my class."

 

Ellen smiled, "Well, what's her name? What is she like?"

 

"Rachel... she's really smart and sweet and has nice handwriting. We work in groups together a lot because we're the top students in the class."

 

"That's great, Sam, she sounds really nice. Have you tried talking to her?"

 

"I can't...." He sighed, "It doesn't come easy to me like it does to Dean. Every time I try to talk to her about anything other than school... I get choked up."

 

"Have you tried asking Dean for advice? I mean he got me to like him, he must be pretty damn charming." She joked.

 

"No... it's embarrassing..."

 

"Sam, he's your big brother. It's his job to teach you things and I'm more than certain he would love to."

 

"Yeah, I guess so... thank you." He smiled at Ellen and she pulled him into a hug.

 

Shortly after, Sam returned to his spot on the couch, peering out the window to see if his brother was back yet. Luckily for him, they were already on the porch. 

 

"Hey, Dean?" He interrupted as he stepped outside, "Can I talk to you for a second?"

 

"What's up?"

 

"Um... it's about a girl, can we talk in private?"

 

Jo smiled, "Oooh~ do you have a crush on someone?"

 

Sam blushed, looking down at his shoes.

 

"Sit down, Sammy. We can help." Dean scooched over, patting the weathered wood of the patio step.

 

He did as his brother told, and Dean continued, "Look, I know you wanted to talk to me alone, and we still can, but since Jo  _is_  a girl, her advice is about as good as mine."

 

Sam nodded, "There's this girl in my class... and I have no idea how to talk to her... I mean, if we're working on an assignment, I do fine, but..." He groaned, putting his face in his hands at his knees, "How do you do it?"

 

"Well, first things first, find out what she's really interested in. Ask her about it. You don't need to pretend that you know everything about it, but just listen."

 

Jo smiled softly, placing her hand on his back. Honestly, she half expected him to say something a little... typical like a cheesy line or something. She shook the thought out of her head, guilty for even thinking it. "He's right, taking an interest in what she likes shows that you care about her as a person, not just that she's pretty to look at." 

 

"Okay... but how do I get from there to her being my girlfriend?" 

 

Dean grinned, "Easy, tiger." He interjected, though he was a bit proud. "One step at a time. Get to know her first." 

 

"I hope you take bigger steps than your brother here, it took him  _twelve years_ to ask me to be his girlfriend." Jo poked, getting a laugh out of Sam.

 

Dean couldn't help but smile, albeit embarrassed, "It would've been _way_ less romantic if I asked you when we were four."

 

"True... I didn't like you yet."

 

"When did you start liking me?" 

 

"Hmm... about 5 seconds before you kissed me."

 

He furrowed his brows, "Seriously?" He asked completely in earnest, and Jo couldn't help but laugh.

 

"No." She pushed herself off the step on her feet, "Let's go inside."

 

Dean got on his feet as well, "Come on, I told you mine. It can't be more embarrassing than that."

 

She gave him a quick glance before turning on her heels and stepping inside. He shrugged it off, and decided to go inside too, she probably just didn't want to say it in front of Sam.

 

"Dean, wait." Sam said before he could leave.

 

He stopped, turning to face his brother.

 

"Is there anything else I should know? That you couldn't say in front of Jo?"

 

Dean chuckled, raising his eyebrows, "Whoa, what exactly do you want to do with this girl?"

 

Sam rolled his eyes, ignoring the heat rising in his cheeks, "Shut up, you know what I mean!"

 

"Okay, okay. Let me think..."


	12. Part 4: Risky Business

Dean laid in bed, staring up at the ceiling for what felt like hours. The lights were off, Sam was asleep, but he was still wide awake. Maybe it was the fact that his girlfriend was across the hall from him. He wanted to talk to her. Kiss her. And..... well, unfortunately this wasn't a high school movie and he would get caught and be in serious trouble. Still... it kept him awake.

Finally, he swung his legs off the bed and, as quietly as possible, tip-toed to Jo's room. Turning the handle first before pushing it open, so as to not make any noise, then stepping inside. Doing the same strategy, he shut it behind him.

Fortunately, Jo was awake too. She set her book on the bed beside her, "What are you doing in here?"

"I couldn't sleep." He was about to take a step forward but stopped himself, "Do you mind if I hang out for a bit?"

"Of course." Jo scooched over, making room for him to sit.

He sat beside her, "What are you reading?"

"Pride and Prejudice."

"Ah. For school or for pleasure?"

"Can't it be both?"

He shrugged, "I guess. Takes the pleasure out of it when you have to write a stuffy report about it."

"True..." she chuckled.

A silence followed, Jo knew whether or not to keep reading and Dean didn't know what to do at all. His gaze jumped from his hands, to her walls, her bookshelf, her tv, and repeat. There was definitely a tension. He wasn't supposed to be in here. Sure, he's been in here plenty of times before, but the fact that Ellen actually knows he's in the house made it a lot more risky.

Jo turned to him. Seeing her movement in his peripheral, he did the same.

"Why did you come in here?" She asked, honestly. "I don't mind, you're just... quiet."

It was a fair question, though a question he didn't want to answer. "Um..." He swallowed, his mouth becoming increasingly dry, "I was thinking about you."

Jo quirked an eyebrow at him with a tinge of a smirk, "Oh yeah?"

Shit. He couldn't help himself now. His eyes scanned her features before falling to her lips. Without a second thought, he closed the distance between them.

She smiled against his mouth and placed her hand on his neck, pulling him closer. Dean placed a hand just above her hip, and Jo's heart picked up the tempo. Dean glided the tip of his tongue across her bottom lip, leaving a tingling sensation in his wake. She parted her lips, sliding her tongue into his mouth as he followed suit.

Jo gripped the hem of his shirt for a second before sliding her hands up his chest. A chill ran up his spine and he moaned at her touch. She slid up his shoulders before slowly trickling down, only to slide up again. He pulled away for a second to remove his shirt before crashing his lips to hers again. Jo lifted her right leg, planting it in between both of his. Her hand made it's way into his thick hair, the other rested on his left thigh.

Dean exhaled at the touch of her hand, and his jeans began to grow even tighter. She was hovering over him now; his heart raced, as did hers.

Tongues wrestling against each other again, he slid one hand underneath her shirt, his hand hot against her skin. He ran it over one cup of her bra,

Ellen swung the door open, intending to ask what Jo was still doing up, instead seeing the scene before her.

"JOANNA BETH HARVELLE, YOU GET OFF THAT BOY RIGHT NOW."

Jo pushed herself upright, "MOM I-I-"

"SAVE IT! Dean Winchester if you value your life you will put your shirt back on and get out of this room, right this instant."

Dean did as she told, exiting the room as quickly as possible and shutting the door behind himself. He knew she'd want to talk to him too, so he leaned against the outer wall of her room. His mind was scrambling. Fuck. He didn't mean for this to happen. HOW did this happen. It was all so fast...

"You mind telling me what the hell that was?" Ellen asked, fuming. All she was missing was steam coming out of her ears.

"He couldn't sleep and we were just kissing!"

"Just kissing? Sweetheart, if I came in five minutes later you could've been pregnant."

Jo's cheeks quickly turned red, "We weren't going to do _that!_ "

"Then would you mind explaining to me what you were doing over him, while he's shirtless, with your hand on his thigh?"

Jo opened her mouth but the words didn't come. What could she say? For all she knows, her mother was right. It was moving so fast, it probably would've headed there.

Dean could hear every word through the wall and he knew what's coming for him is going to be a hell of a lot worse. He slid down the wall till he was sitting on the floor. Nausea grew in his chest. He should've stayed in bed. Why didn't he stay in bed. _Why didn't he stay in bed?_

Sam stepped out of their guest bedroom, "What's going on?"

"Nothing. Go back to bed."

"I heard Ellen shouting."

"Sam, please. I can't talk about it right now just go to bed." Dean pleaded.

Sam was more confused than ever, but he did as he was told and returned to bed.

Ellen opened Jo's door just then, "Dean, come in here."

He swallowed hard, using his clammy palms to push himself onto his feet and went inside.

Ellen closed the door, "Sit down."

Dean sat beside Jo on the bed.

"I had ONE rule when you first got here. THIS MORNING, I might add. What was that rule?"

"No fooling around." Dean answered.

"So you didn't forget." Ellen stated pointedly. "So, Jo said you couldn't sleep, so you came in her room. Why?"

"I..I was thinking about her and wanted to see her."

"Oh, and you did plenty more than that, didn't you?"

Dean remained silent, as did Jo.

"Jo, could you give us a minute?"

"No, whatever you want to say to him you can say in front of me."

"Joanna. _Now._ " Ellen affirmed.

Jo reluctantly did as she was told, and waited outside as Dean did.

Ellen walked up to him, he instinctively stood up to meet her eyes.

"I am _furious_ with you. Do you have any idea how much trust I put in you since you started dating my daughter? Since I let you into my home this weekend? And what did you do? Sneak around while I'm asleep so you can have sex with my daughter?"

"I-I'm sorry I didn't mean-"

"You didn't MEAN to? Well that just fixes everything, doesn't it?"

His eyes started to get misty but he fought it back best he could. "Ellen, I swear I just came in here for some company since she was awake too. I sat next to her and we started kissing and the next thing I knew, you came in. But nothing was going to happen, I promise! Jo isn't ready for that, she's told me so."

Ellen let out a long sigh, "I'm still furious with you. And I'm calling your father."

 _Oh fuck, he forgot about that part._ "Ellen please, don't call him, he'll never let me see her again." Dean begged, a tear streaming down his cheek despite his best efforts.

"Well I'm not sure I disagree with that right now."

"Ellen, _please._ " The floodgates were open now and it was making it very hard for her to be objective.

"I won't call him, under one condition. If anything like this happens again, or you even do something you're not supposed to with Jo; at home, here, or at school, I'm telling him."

Dean exhaled out of relief, "Agreed."

"Now you go to bed right now and you STAY in bed, understand?"

"Yes ma'am."

Dean promptly returned to his bedroom, throwing the sheets back and tucking himself in them.

"Dean?" Sam asked, "What happened?"

"It's over, and we're not going to talk about it again." Dean turned on his side, closing his eyes.

"But-"

"Goodnight, Sam."

His little brother groaned, laying his head back to the pillow, "Goodnight... jerk."

"Bitch."

"Hey!"

Dean laughed and Sam threw his spare pillow at his brother's head.

**Author's Note:**

> Hey, guys!! Please let me know what you think!!
> 
> If you have a favorite part or any suggestions, leave me a comment! I'll read and reply to all!


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